Multicyclic aromatic compound and organic light emitting device using the same

ABSTRACT

The present specification describes a multicyclic aromatic ring compound having a novel structure and an organic light emitting device using the same.

FIELD OF THE INVENTION

The present invention relates to a novel multicyclic aromatic compoundand an organic light emitting device using the same.

BACKGROUND OF THE INVENTION

An electroluminescent device is one type of self-luminescent-typedisplay devices, and has advantages in that it has a wide viewing angle,an excellent contrast, and quick response time.

An organic light emitting device has a structure in which an organicthin film is disposed between two electrodes. When voltage is applied toan organic light emitting device having such a structure, light emits byelectrons and holes injected from the two electrodes being dissipatedafter the electrons and holes make a pair by bonding in the organic thinfilm. The organic thin film may be formed as a monolayer or a multilayeras necessary.

Materials of an organic thin film may have a light emitting functionwhen necessary. For example, as the material of an organic thin film,compounds capable of forming a light emitting layer alone may be used,or compounds capable of performing as a host or a dopant of ahost-dopant-based light emitting layer may also be used. In addition tothese, compounds capable of performing hole injection, hole transfer,electron blocking, hole blocking, electron transfer, electron injection,or the like, may also be used as the material of an organic thin film.

There have been continuous demands for the development of organic thinfilm materials in order to improve the performance, life span orefficiency of an organic light emitting device.

For example, CBP has been mostly widely known so far as a host materialof a phosphorescent light emitting body, and an organic light emittingdevice in which a hole blocking layer such as BCP and BAlq is applied,and an organic light emitting device in which BAlq derivatives are usedas a host are well known.

However, existing materials have advantages in the aspect of lightemitting properties, but have disadvantages such that the materialschange when going through a high-temperature deposition process undervacuum due to a low glass transition temperature and very low thermalstability. In an organic light emitting device, powerefficiency=(n/voltage)×current efficiency, therefore, power efficiencyis inversely proportional to voltage, and power efficiency needs to behigh in order to have low power consumption of the organic lightemitting device. In fact, an organic light emitting device that uses aphosphorescent light emitting material has quite high current efficiency(cd/A) compared to an organic light emitting device that uses afluorescent light emitting material, however, when existing materialssuch as CBP or BAlq are used as the host of a phosphorescent lightemitting material, there are no huge advantages in terms of powerefficiency (lm/w) since driving voltage is high compared to that of anorganic light emitting device using a fluorescent material. In addition,the life span of an organic light emitting device is not at allsatisfactory, therefore, there have been demands for the development ofhost materials that are more stable and show more excellentperformances.

SUMMARY OF THE INVENTION

The present invention provides a novel multicyclic aromatic compound andan organic light emitting device using the same.

The present invention provides a compound of the following ChemicalFormula 1:

In Chemical Formula 1,

R₁ and R₂ are each independently hydrogen; halogen; substituted orunsubstituted C₁-C₃₀ alkyl; substituted or unsubstituted C₆-C₃₀ aryl;substituted or unsubstituted C₆-C₃₀ aryl in which one or more ofsubstituted or unsubstituted C₃-C₃₀ cycloalkyl, substituted orunsubstituted C₃-C₃₀ heteroaryl and substituted or unsubstituted5-membered to 7-membered heterocycloalkyl are fused; substituted orunsubstituted C₃-C₃₀ heteroaryl; substituted or unsubstituted C₃-C₃₀heteroaryl in which one or more of substituted or unsubstituted C₃-C₃₀cycloalkyl, a substituted or unsubstituted C₆-C₃₀ aromatic ring andsubstituted or unsubstituted 5-membered to 7-membered heterocycloalkylare fused; substituted or unsubstituted 5-membered to 7-memberedheterocycloalkyl; substituted or unsubstituted 5-membered to 7-memberedheterocycloalkyl in which one or more of substituted or unsubstitutedC₃-C₃₀ heterocycloalkyl, a substituted or unsubstituted C₆-C₃₀ aromaticring and substituted or unsubstituted C₃-C₃₀ heteroaryl are fused;substituted or unsubstituted C₃-C₃₀ cycloalkyl; substituted orunsubstituted C₃-C₃₀ cycloalkyl in which one or more of substituted orunsubstituted C₃-C₃₀ heterocycloalkyl, a substituted or unsubstitutedC₆-C₃₀ aromatic ring and substituted or unsubstituted C₃-C₃₀ heteroarylare fused; cyano; —NR₁₁R₁₂; —SiR₁₃R₁₄R₁₅; —OR₁₆; —SR₁₇; substituted orunsubstituted (C₆-C₃₀)ar(C₁-C₃₀)alkyl; substituted or unsubstitutedalkylamino; C₃-C₃₀ heteroaryl in which —SiR₁₈R₁₉R₂₀ is substituted;substituted or unsubstituted C₆-C₃₀ arylamino; substituted orunsubstituted C₂-C₃₀ alkenyl; substituted or unsubstituted C₂-C₃₀alkynyl; carboxyl; nitro or hydroxy; or may form a monocyclic ormulticyclic aliphatic ring, or a monocyclic or multicyclic aromaticring, by being linked to an adjacent substituent through C₃-C₃₀ alkyleneor C₃-C₃₀ alkenylene that does or does not include a fused ring;

R₁₁ to R₂₀ are each independently hydrogen; substituted or unsubstitutedalkyl; substituted or unsubstituted C₆-C₃₀ aryl; or substituted orunsubstituted C₃-C₃₀ heteroaryl, or may form a monocyclic or multicyclicaliphatic ring, or a monocyclic or multicyclic aromatic ring, by beinglinked to an adjacent substituent through C₃-C₃₀ alkylene or C₃-C₃₀alkenylene that does or does not include a fused ring;

the heterocycloalkyl and heteroaryl include one or more heteroatomsselected from N, O, S and Si;

R₃ to R₁₀ are each independently hydrogen or a monovalent organicsubstituent,

R₃ and R₄, R₄ and R₅, R₅ and R₆, R₇ and R₈, R₈ and R₉ or R₉ and R₁₀ mayform a monocyclic or multicyclic aliphatic ring, or a monocyclic ormulticyclic aromatic ring, by being linked through C₃-C₃₀ alkylene orC₃-C₃₀ alkenylene that does or does not include a fused ring.

The present invention also provides an organic light emitting devicethat includes a first electrode, a second electrode, and one or moreorganic material layers provided between the first electrode and thesecond electrode, wherein one or more layers of the organic materiallayers include the compound of Chemical Formula 1.

According to one embodiment, the organic material layer that includesthe compound of Chemical Formula 1 is a light emitting layer.

According to another embodiment, the organic material layer thatincludes the compound of Chemical Formula 1 further includes a lightemitting dopant.

According to still another embodiment, the organic material layer thatincludes the compound of Chemical Formula 1 further includes aphosphorescent dopant.

ADVANTAGEOUS EFFECTS

A Compound according to the present invention may be used as thematerial of an organic material layer of an organic light emittingdevice. The compound may be used as a hole injection material, a holetransfer material, a light emitting material, an electron transfermaterial, an electron injection material or the like in an organic lightemitting device. In particular, the compound may be used as a lightemitting material of an organic light emitting device. In addition, thecompound may be used as a host material, particularly, a phosphorescenthost material of the light emitting layer of an organic light emittingdevice.

When the compound according to the present invention is used as a lightemitting material, there are advantages in that the material hasexcellent light emitting efficiency compared to existing materials, longlife span of a device can be expected due to excellent life spanproperties of the material, and an organic light emitting device havingimproved power consumption can be manufactured by inducing theenhancement of power efficiency. In addition, the compound canaccomplish appropriate color coordinates. Therefore, by using thecompound according to the present invention, an organic light emittingdevice having high efficiency and long life span can be provided.

BRIEF DESCRIPTION OF THE DRAWINGS

FIGS. 1 to 3 illustrate the laminating order of electrodes and organicmaterial layers of an organic light emitting device according toembodiments of the present invention.

DETAILED DESCRIPTION OF THE EMBODIMENTS

Hereinafter, the present invention will be described in detail.

A compound according to the present invention may be represented byChemical Formula 1. The compound according to the present invention maybe used as the material of an organic material layer of an organic lightemitting device depending on the structural and physical properties of acore structure. Specifically, Chemical Formula 1 has dibenzopentalene asthe core structure. Dibenzopentalene is an antiaromatic molecule havinga pentalene skeleton. According to a Hückel rule, all the carbonmolecules within the skeleton share π electrons, and the molecule having4n number of π electrons has ‘antiaromaticity’, and in this structure,reactivity improves due to the mobility improvement of the π electronswithin the structure having a covalent bonding. In addition, themolecule can have aromaticity with excellent stability due to easymodification to a divalent anion form. Furthermore, the molecule havingpentalene as a skeleton has high stability disregard of itsantiaromaticity, therefore, the molecule is useful in preparingtransition metal complexes having a sandwich form, and is useful as thematerial of an organic semiconductor or a dye having highoxidation/reduction potential as a n electron conjugation moleculehaving a trapezoid form. In this respect, the core structure of ChemicalFormula 1 is different from the structure of dihydropentalene at theposition of π electrons as shown below.

In “substituted or unsubstituted” of R₁ to R₁₀, substituted means beingeach independently further substituted with one or more selected fromthe group consisting of deuterium, halogen, C₁-C₃₀ alkyl in whichhalogen is substituted or unsubstituted, C₆-C₃₀ aryl, C₃-C₃₀ heteroarylin which C₆-C₃₀ aryl is substituted or unsubstituted, 5-membered to7-membered heterocycloalkyl, 5-membered to 7-membered heterocycloalkylin which one or more aromatic rings are fused, C₃-C₃₀ cycloalkyl, C₃-C₃₀cycloalkyl in which one or more aromatic rings are fused,tri(C₁-C₃₀)alkylsilyl, di(C₁-C₃₀)alkyl(C₆-C₃₀)arylsilyl,tri(C₆-C₃₀)arylsilyl, C₂-C₃₀ alkenyl, C₂-C₃₀ alkynyl, cyano, carbazolyl,—NR₃₁R₃₂, —SiR₃₃R₃₄R₃₅, —OR₃₆, SR₃₇, (C₆-C₃₀)ar(C₁-C₃₀)alkyl,(C₁-C₃₀)alkyl(C₆-C₃₀)aryl, alkyloxy, alkylthio, C₆-C₃₀ aryloxy, C₆-C₃₀arylthio, carboxyl, nitro or hydroxy, and R₃₁ to R₃₇ are eachindependently hydrogen, C₁-C₃₀ alkyl, C₆-C₃₀ aryl or C₃-C₃₀ heteroaryl,or may form a monocyclic or multicyclic aliphatic ring, or a monocyclicor multicyclic aromatic ring, by being linked to an adjacent substituentthrough C₃-C₃₀ alkylene or C₃-C₃₀ alkenylene that does or does notinclude a fused ring.

The substituent including “alkyl”, “alkoxy” and additional “alkyl”parts, which is described in the present specification, includes alllinear or branched forms.

In the present specification, cycloalkyl includes monocyclic ormulticyclic having 3 to 30 carbon atoms, and specifically, includes allsubstituted or unsubstituted adamantyl, or substituted or unsubstitutedC₇-C₃₀ bicycloalkyl. Herein, multicyclic means a group in whichcycloalkyl is directly bonded to or condensed with other ring groups.Herein, the other ring groups may be cycloalkyl, but may also be othertypes of ring groups, for example, heterocycloalkyl, an aromatic ring,heteroaryl or the like. The number of cycloalkyl carbon atoms may be 3to 30, specifically 3 to 20, and more specifically 5 to 12.

In the present specification, heterocycloalkyl includes S, O or N as aheteroatom, includes monocyclic or multicyclic having 2 to 30 carbonatoms, and may be further substituted with other substituents. Hereinmulticyclic means a group in which heterocycloalkyl is directly bondedto or condensed with other ring groups. Herein, the other ring groupsmay be heterocycloalkyl, but may also be other types of ring groups, forexample, cycloalkyl, an aromatic ring, heteroaryl or the like. Thenumber of heterocycloalkyl carbon atoms may be 2 to 30, specifically 2to 20, and more specifically 3 to 12.

In the present specification, aryl is an organic radical derived fromaromatic hydrocarbon by removing one hydrogen, and includes a single orfused ring including a 4-membered to 7-membered ring and more preferablya 5-membered or 6-membered ring, and also includes a structure in whichone or more aryl are bonded through chemical bonding. Specific examplesof the aryl include phenyl, naphthyl, biphenyl, anthryl, indenyl,fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl,naphthacenyl, fluoranthenyl, or the like, but are not limited thereto.

In the present specification, heteroaryl means an aryl group in which 1to 4 heteroatoms selected from N, O and S are included as an aromaticring skeleton atoms, and the rest of the aromatic ring skeleton atoms iscarbon, and includes 5- to 6-membered monocyclic heteroaryl ormulticyclic heteroaryl condensed with one or more benzene rings, and maybe partially saturated. In addition, the heteroaryl in the presentspecification also includes a structure in which one or more heteroarylare bonded through chemical bonding. The heteroaryl group includes adivalent aryl group in which the heteroatom within the ring is oxidizedor becomes 4-membered, and for example, an N-oxide or quaternary salt isformed. Specific examples of the heteroaryl includes moonocyclicheteroaryl such as furyl, thienyl, pyrolyl, imidazolyl, pyrazolyl,thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl,oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl,pyridyl, pyrazinyl, pyrimidinyl or pyridazinyl, multicyclic heteroarylsuch as benzofuryl, benzothienyl, isobenzofuryl, benzoimidazolyl,benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl,isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl,isoquinolyl, cinnolinyl, quinazolinyl, quinolizinyl, quinoxalinyl,carbazolyl, phenanthridinyl or benzodioxolyl, a corresponding N-oxidethereof such as pyridyl N-oxide or quinolyl N-oxide, a quaternary saltthereof, or the like, but are not limited thereto.

In addition, a “C₁-C₃₀ alkyl” group described in the presentspecification includes C₁-C₂₀ alkyl or C₁-C₁₀ alkyl, a “C₆-C₃₀ aryl”group includes C₆-C₂₀ aryl or C₆-C₁₂ aryl. A “C₃-C₃₀ heteroaryl” groupincludes C₃-C₂₀ heteroaryl or C₃-C₁₂ heteroaryl, a “C₃-C₃₀ cycloalkyl”group includes C₃-C₂₀ cycloalkyl or C₃-C₇ cycloalkyl. A “C₂-C₃₀ alkenylor alkynyl” group includes C₂-C₂₀ alkenyl or alkynyl, or C₂-C₁₀ alkenylor alkynyl.

In the present specification, halogen includes F, Cl, Br and I.

According to one embodiment of the present invention, R₁ to R¹⁰ are eachindependently hydrogen, halogen, substituted or unsubstituted C₁-C₃₀alkyl, substituted or unsubstituted C₆-C₃₀ aryl, substituted orunsubstituted C₆-C₃₀ aryl in which one or more substituted orunsubstituted C₃-C₃₀ cycloalkyls are fused, substituted or unsubstitutedC₃-C₃₀ heteroaryl, substituted or unsubstituted 5-membered to 7-memberedheterocycloalkyl, 5-membered to 7-membered heterocycloalkyl in which oneor more substituted or unsubstituted aromatic rings are fused,substituted or unsubstituted C₃-C₃₀ cycloalkyl, C₃-C₃₀ cycloalkyl inwhich one or more substituted or unsubstituted aromatic rings are fused,cyano, —NR₁₁R₁₂, —SiR₁₃R₁₄R₁₅, —OR₁₆, —SR₁₇, substituted orunsubstituted (C₆-C₃₀)ar(C₁-C₃₀)alkyl, substituted or unsubstitutedalkylamino, C₃-C₃₀ heteroaryl in which —SiR₁₈R₁₉R₂₀ is substituted,substituted or unsubstituted C₆-C₃₀ arylamino, substituted orunsubstituted C₂-C₃₀ alkenyl, substituted or unsubstituted C₂-C₃₀alkynyl, carboxyl, nitro or hydroxy, or may form a monocyclic ormulticyclic aliphatic ring, or a monocyclic or multicyclic aromaticring, by being linked to an adjacent substituent through C₃-C₃₀ alkyleneor C₃-C₃₀ alkenylene that does or does not include a fused ring;

R₁₁ to R₂₀ are each independently substituted or unsubstituted C₁-C₃₀alkyl, substituted or unsubstituted C₆-C₃₀ aryl or substituted orunsubstituted C₃-C₃₀ heteroaryl, or may form a monocyclic or multicyclicaliphatic ring, or a monocyclic or multicyclic aromatic ring, by beinglinked to an adjacent substituent through (C₃-C₃₀)alkylene or(C₃-C₃₀)alkenylene that does or does not include a fused ring; theheterocycloalkyl and heteroaryl include one or more heteroatoms selectedfrom N, O, S and Si.

According to one embodiment of the present invention, R₁ to R₁₀ are eachindependently selected from hydrogen, halogen, alkyl such as methyl,ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl or octyl, arylsuch as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl,pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl ortriphenylenyl, aryl in which one or more cycloalkyl are fused, such as1,2-dihydroacenaphthyl, heteroaryl such as dibenzothiophenyl,dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl,pyrimidinyl, pyridazinyl, quinoxalinyl or phenanthrolinyl,heterocycloalkyl in which one or more aromatic rings are fused, such asbenzopyrrolidino, benzopiperidino, dibenzomorpholino or dibenzoazepino,or amino in which aryl such as phenyl, naphthyl, fluorenyl, biphenyl,phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl,fluoranthenyl, chrysenyl or triphenylenyl, or heteroaryl such asdibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl,quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl,phenanthrolinyl is substituted, aryloxy such as biphenyloxy, arylthiosuch as biphenylthio, aralkyl such as biphenylmethyl or triphenylmethyl,carboxyl, nitro or hydroxy, but R₁ to R₁₀ are not limited thereto, andmay be further substituted as in Chemical Formula 1.

According to one embodiment of the present invention, R₁ and R₂ are eachindependently halogen; substituted or unsubstituted C₁-C₃₀ alkyl;substituted or unsubstituted C₆-C₃₀ aryl; substituted or unsubstitutedC₆-C₃₀ aryl in which one or more of substituted or unsubstituted C₃-C₃₀cycloalkyl, substituted or unsubstituted C₃-C₃₀ heteroaryl andsubstituted or unsubstituted 5-membered to 7-membered heterocycloalkylare fused; substituted or unsubstituted C₃-C₃₀ heteroaryl; substitutedor unsubstituted C₃-C₃₀ heteroaryl in which one or more of substitutedor unsubstituted C₃-C₃₀ cycloalkyl, a substituted or unsubstitutedC₆-C₃₀ aromatic ring and substituted or unsubstituted 5-membered to7-membered heterocycloalkyl are fused; substituted or unsubstituted5-membered to 7-membered heterocycloalkyl; substituted or unsubstituted5-membered to 7-membered heterocycloalkyl in which one or more ofsubstituted or unsubstituted C₃-C₃₀ heterocycloalkyl, a substituted orunsubstituted C₆-C₃₀ aromatic ring and substituted or unsubstitutedC₃-C₃₀ heteroaryl are fused; substituted or unsubstituted C₃-C₃₀cycloalkyl; substituted or unsubstituted C₃-C₃₀ cycloalkyl in which oneor more of substituted or unsubstituted C₃-C₃₀ heterocycloalkyl, asubstituted or unsubstituted C₆-C₃₀ aromatic ring and substituted orunsubstituted C₃-C₃₀ heteroaryl are fused; cyano; —NR₁₁R₁₂; —OR₁₆;—SR₁₇; substituted or unsubstituted (C₆-C₃₀)ar(C₁-C₃₀)alkyl; substitutedor unsubstituted alkylamino; C₃-C₃₀ heteroaryl in which —SiR₁₈R₁₉R₂₀ issubstituted; substituted or unsubstituted C₆-C₃₀ arylamino; substitutedor unsubstituted C₂-C₃₀ alkenyl; substituted or unsubstituted C₂-C₃₀alkynyl; carboxyl; nitro or hydroxy; or may form a monocyclic ormulticyclic aliphatic ring, or a monocyclic or multicyclic aromaticring, by being linked to an adjacent substituent through C₃-C₃₀ alkyleneor C₃-C₃₀ alkenylene that does or does not include a fused ring.

According to one embodiment of the present invention, at least one of R₁and R₂ has seven or more carbons in ring members.

According to one embodiment of the present invention, at least one of R₁and R₂ includes two or more rings.

According to one embodiment of the present invention, R₁ and R₂ aredifferent from each other.

According to one embodiment of the present invention, at least one of R₁and R₂ is C₁-C₃₀ alkyl.

According to one embodiment of the present invention, R₁ and R₂ may beselected from hydrogen, alkyl, phenyl, naphthyl, anthracenyl,phenanthrenyl, pyrenyl, phenyl- or alkyl-substituted fluorenyl,phenyl-substituted or unsubstituted carbazolyl, naphthyl-substitutedphenyl, biphenyl, indenyl, acenaphthylenyl, fluoranthenyl,phenyl-substituted naphthyl, indolyl, benzoxazolyl, benzothiazolyl andarylamine-substituted phenyl.

According to one embodiment of the present invention, R₁ and R₂ may beselected from alkyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl,phenyl- or alkyl-substituted fluorenyl, phenyl-substituted orunsubstituted carbazolyl, naphthyl-substituted phenyl, biphenyl,indenyl, acenaphthylenyl, fluoranthenyl, phenyl-substituted naphthyl,indolyl, benzoxazolyl, benzothiazolyl and arylamine-substituted phenyl.

In Chemical Formula 1, R₃ to R₁₀ are each independently hydrogen; or amonovalent organic substituent. As specific examples, R₃ to R₁₀ are eachindependently hydrogen; halogen; substituted or unsubstituted C₁-C₃₀alkyl; substituted or unsubstituted C₆-C₃₀ aryl; substituted orunsubstituted C₆-C₃₀ aryl in which one or more of substituted orunsubstituted C₃-C₃₀ cycloalkyl, substituted or unsubstituted C₃-C₃₀heteroaryl and substituted or unsubstituted 5-membered to 7-memberedheterocycloalkyl are fused; substituted or unsubstituted C₃-C₃₀heteroaryl; substituted or unsubstituted C₃-C₃₀ heteroaryl in which oneor more of substituted or unsubstituted C₃-C₃₀ cycloalkyl, a substitutedor unsubstituted C₆-C₃₀ aromatic ring and substituted or unsubstituted5-membered to 7-membered heterocycloalkyl are fused; substituted orunsubstituted 5-membered to 7-membered heterocycloalkyl; substituted orunsubstituted 5-membered to 7-membered heterocycloalkyl in which one ormore of substituted or unsubstituted C₃-C₃₀ heterocycloalkyl, asubstituted or unsubstituted C₆-C₃₀ aromatic ring and substituted orunsubstituted C₃-C₃₀ heteroaryl are fused; substituted or unsubstitutedC₃-C₃₀ cycloalkyl; substituted or unsubstituted C₃-C₃₀ cycloalkyl inwhich one or more of substituted or unsubstituted C₃-C₃₀heterocycloalkyl, a substituted or unsubstituted C₆-C₃₀ aromatic ringand substituted or unsubstituted C₃-C₃₀ heteroaryl are fused; cyano;—NR₁₁R₁₂; —SiR₁₃R₁₄R₁₅; —OR₁₆; —SR₁₇; substituted or unsubstituted(C₆-C₃₀)ar(C₁-C₃₀)alkyl; substituted or unsubstituted C₁-C₃₀ alkylamino;C₃-C₃₀ heteroaryl in which —SiR₁₈R₁₉R₂₀ is substituted; substituted orunsubstituted C₆-C₃₀ arylamino; substituted or unsubstituted C₂-C₃₀alkenyl; substituted or unsubstituted C₂-C₃₀ alkynyl; carboxyl; nitro orhydroxy; or may form a monocyclic or multicyclic aliphatic ring, or amonocyclic or multicyclic aromatic ring, by being linked to an adjacentsubstituent through C₃-C₃₀ alkylene or C₃-C₃₀ alkenylene that does ordoes not include a fused ring.

According to one embodiment of the present invention, R₃ to R₁₀ are eachindependently hydrogen; substituted or unsubstituted alkyl; substitutedor unsubstituted C₆-C₃₀ aryl; or may form a monocyclic or multicyclicaliphatic ring, or a monocyclic or multicyclic aromatic ring, by beinglinked to an adjacent substituent through C₃-C₃₀ alkylene or C₃-C₃₀alkenylene that does or does not include a fused ring.

According to one embodiment of the present invention, R₃ to R₁₀ are eachindependently hydrogen; methyl or phenyl, or may form a phenyl groupwith an adjacent substituent.

According to one embodiment of the present invention, R₅ and R₉ are eachindependently hydrogen; methyl or phenyl, or form a phenyl group with anadjacent substituent, and R₃, R₄, R₆, R₇, R₈ and R₁₀ are hydrogen.

According to one embodiment of the present invention, R₄, R₅, R₈ and R₉are each independently hydrogen; methyl or phenyl, or form a phenylgroup with an adjacent substituent, and R₃, R₆, R₇ and R₁₀ are hydrogen.

According to one embodiment of the present invention, Chemical Formula 1may be represented by any one of Chemical Formulae 2 to 9.

In Chemical Formulae 2 to 9,

R₁, R₂, R₃ and R₄ are the same as those defined in claim 1,

p and q each independently represent an integer of 1 to 4,

Y1 to Y4 represent one of substituted or unsubstituted C₃-C₃₀cycloalkyl, substituted or unsubstituted C₃-C₃₀ heteroaryl, substitutedor unsubstituted 5-membered to 7-membered heterocycloalkyl andsubstituted or unsubstituted C₆-C₃₀ aryl, or a ring in which two or moreof these rings are fused.

According to one embodiment, Chemical Formula 1 may be illustrated bythe following structural formulae, however, the scope of the presentinvention is not limited thereto.

The compounds described in the present specification may be preparedwith reference to preparation examples described later.

The present invention also provides an organic light emitting devicethat includes a first electrode, a second electrode, and one or moreorganic material layers provided between the first electrode and thesecond electrode, wherein one or more layers of the organic materiallayers include the compound of Chemical Formula 1.

The laminating order of the electrodes and the organic material layersof the organic light emitting device according to embodiments of thepresent invention is illustrated in FIGS. 1 to 3. However, thesediagrams are not intended to limit the scope of the present invention,and the structures of organic light emitting devices known in therelated art may also be applied to the present invention.

According to FIG. 1, an organic light emitting device in which an anode(200), an organic material layer (300) and a cathode (400) are laminatedon a substrate (100) in consecutive order is shown by the diagram.However, the structure of the organic light emitting device is notlimited to this structure only, and as shown in FIG. 2, an organic lightemitting device in which a cathode, an organic material layer and ananode are laminated on a substrate in consecutive order may be included.

FIG. 3 illustrates the case in which the organic material layer is amultilayer. An organic light emitting device according to FIG. 3includes a hole injection layer (301), a hole transfer layer (302), alight emitting layer (303), an electron transfer layer (304) and anelectron injection layer (305). However, the scope of the presentinvention is not limited to this laminated structure, and whennecessary, other layers except a light emitting layer may not beincluded, and other necessary layers having other functions may beadded.

An organic light emitting device according to the present invention maybe prepared using methods known in the related art except that thecompound of Chemical Formula 1 is included in one or more layers of theorganic material layers.

The compound of Chemical Formula 1 may form one or more layers of theorganic material layers alone in the organic light emitting device.However, when necessary, the compound of Chemical Formula 1 may form theorganic material layers by being mixed with other materials.

The compound of Chemical Formula 1 may be used as a hole injectionmaterial, a hole transfer material, a light emitting material, anelectron transfer material, an electron injection material or the likein an organic light emitting device. Particularly, the compound ofChemical Formula 1 may be used as a light emitting material of anorganic light emitting device, specifically as a host material of thelight emitting layer, and particularly, as a phosphorescent hostmaterial, and in this case, an organic light emitting device having highefficiency and long life span can be provided. According to one specificexample, the compound of Chemical Formula 1 may be used as a fluorescentblue host material.

According to one embodiment, the compound of Chemical Formula 1 mayparticularly function as an organic light emitting compound, therefore,the organic material layer that includes the compound of ChemicalFormula 1 is a light emitting layer.

According to another embodiment, the compound of Chemical Formula 1 mayfunction as a light emitting host material, therefore, the organicmaterial layer that includes the compound of Chemical Formula 1 furtherincludes a light emitting dopant.

According to another embodiment, the organic material layer thatincludes the compound of Chemical Formula 1 further includes afluorescent dopant.

According to another embodiment, the organic material layer thatincludes the compound of Chemical Formula 1 further includes a bluefluorescent dopant.

According to another embodiment, the organic material layer thatincludes the compound of Chemical Formula 1 further includes aphosphorescent dopant.

The light emitting dopant applied to an organic light emitting device ofthe present invention is not particularly limited, however, thecompounds of the following Chemical Formula 10 may be illustrated.

M¹L¹⁰¹L¹⁰²L¹⁰³  [Chemical Formula 10]

Herein, M¹ is selected from the group consisting of metals of group 7,group 8, group 9, group 10, group 11, group 13, group 14, group 15 andgroup 16, and ligands L¹⁰¹, L¹⁰² and L¹⁰³ are each independentlyselected from the following structures.

In Chemical Formula 10,

R₂₀₁ to R₂₀₃ are each independently hydrogen, deuterium, C₁-C₃₀ alkyl inwhich halogen is substituted or unsubstituted, C₆-C₃₀ aryl in whichC₁-C₃₀ alkyl is substituted or unsubstituted, or halogen;

R₂₀₄ to R₂₁₉ are each independently hydrogen, deuterium, substituted orunsubstituted C₁-C₃₀ alkyl, substituted or unsubstituted alkoxy,substituted or unsubstituted C₃-C₃₀ cycloalkyl, substituted orunsubstituted C₂-C₃₀ alkenyl, substituted or unsubstituted C₆-C₃₀ aryl,substituted or unsubstituted mono- or di-(C₁-C₃₀)alkylamino, substitutedor unsubstituted mono- or di-(C₆-C₃₀)arylamino, SF5, substituted orunsubstituted tri(C₁-C₃₀)alkylsilyl, substituted or unsubstituteddi(C₁-C₃₀)alkyl(C₆-C₃₀)arylsilyl, substituted or unsubstitutedtri(C₆-C₃₀)arylsilyl, cyano, or halogen;

R₂₂₀ to R₂₂₃ are each independently hydrogen, deuterium, C₁-C₃₀ alkyl inwhich halogen is substituted or unsubstituted, C₆-C₃₀ aryl in whichC₁-C₃₀ alkyl is substituted or unsubstituted;

R₂₂₄ and R₂₂₅ are each independently hydrogen, deuterium, substituted orunsubstituted C₁-C₃₀ alkyl, substituted or unsubstituted C₆-C₃₀ aryl, orhalogen, or R₂₂₄ and R₂₂₅ may form a monocyclic or multicyclic aliphaticring, or a monocyclic or multicyclic aromatic ring, by being linkedthrough C₃-C₁₂ alkylene or C₃-C₁₂ alkenylene that does or does notinclude a fused ring;

R₂₂₆ is substituted or unsubstituted C₁-C₃₀ alkyl, substituted orunsubstituted C₆-C₃₀ aryl, substituted or unsubstituted C₃-C₃₀heteroaryl, or halogen;

R₂₂₇ to R₂₂₉ are each independently hydrogen, deuterium, substituted orunsubstituted C₁-C₃₀ alkyl, substituted or unsubstituted C₆-C₃₀ aryl, orhalogen;

R₂₃₀ and R₂₃₁ are each independently hydrogen, C₁-C₂₀ alkyl in whichhalogen is substituted or unsubstituted, C₆-C₂₀ aryl, halogen, cyano,tri(C₁-C₂₀)alkylsilyl, di(C₁-C₂₀)alkyl(C₆-C₂₀)arylsilyl,tri(C₆-C₂₀)arylsilyl, C₁-C₂₀ alkoxy, C₁-C₂₀ alkylcarbonyl, C₆-C₂₀arylcarbonyl, di(C₁-C₂₀)alkylamino or di(C₆-C₂₀)arylamino, or R₂₃₀ andR₂₃₁ form a monocyclic or multicyclic aliphatic ring, or a monocyclic ormulticyclic aromatic ring, by being linked through C₃-C₁₂ alkylene orC₃-C₁₂ alkenylene that does or does not include a fused ring;

The alkyl, aryl, or a monocyclic or multicyclic aliphatic ring or amonocyclic or multicyclic aromatic ring formed by being linked throughC₃-C₁₂ alkylene or C₃-C₁₂ alkenylene that does or does not include afused ring, which are included in R₂₃₀ and R₂₃₁, may be furthersubstituted with one or more substituents selected from C₁-C₂₀ alkyl inwhich halogen is substituted or unsubstituted, halogen, cyano,tri(C₁-C₂₀)alkylsilyl, di(C₁-C₂₀)alkyl(C₆-C₂₀)arylsilyl,tri(C₆-C₂₀)arylsilyl, C₁-C₂₀ alkoxy, C₁-C₂₀ alkylcarbonyl, C₆-C₂₀arylcarbonyl, di(C₁-C₂₀)alkylamino, di(C₆-C₂₀)arylamino, phenyl,naphthyl, anthryl, fluorenyl or spirobifluorenyl, or may be furthersubstituted with phenyl or fluorenyl in which one or more substituentsselected from the group consisting of (C₁-C₂₀)alkyl in which halogen issubstituted or unsubstituted, halogen, cyano, tri(C₁-C₂₀)alkylsilyl,di(C₁-C₂₀)alkyl(C₆-C₂₀)arylsilyl, tri(C₆-C₂₀)arylsilyl, (C₁-C₂₀)alkoxy,(C₁-C₂₀)alkylcarbonyl, (C₆-C₂₀)arylcarbonyl, di(C₁-C₂₀)alkylamino,di(C₆-C₂₀)arylamino, phenyl, naphthyl, anthryl, fluorenyl, andspirobifluorenyl are substituted;

R₂₃₂ to R₂₃₉ are each independently hydrogen, (C₁-C₂₀)alkyl in whichhalogen is substituted or unsubstituted, (C₁-C₂₀)alkoxy,(C₃-C₁₂)cycloalkyl, halogen, cyano, (C₆-C₂₀)aryl, (C₄-C₂₀)heteroaryl,tri(C₁-C₂₀)alkylsilyl, di(C₁-C₂₀)alkyl(C₆-C₂₀)arylsilyl ortri(C₆-C₂₀)arylsilyl; and

Q is

and R₂₄₁ to R₂₅₂ are each independently hydrogen, C₁-C₆₀ alkyl in whichhalogen is substituted or unsubstituted, C₁-C₃₀ alkoxy, halogen, C₆-C₆₀aryl, cyano, C₅-C₆₀ cycloalkyl, or R₂₄₁ to R₂₅₂ may form a C₅-C₇ spiroring or a C₅-C₉ fused ring by being linked to an adjacent substituentthrough alkylene or alkenylene, or may form a C₅-C₇ fused ring by beinglinked to R₂₀₇ or R₂₀₈ through alkylene or alkenylene.

M¹ is selected from Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te,Au and Ag, and the compound of Chemical Formula 10 includes thoseillustrated in Korean Patent Application No. 10-2009-0037519, but is notlimited thereto.

In the organic light emitting device of the present invention, theorganic material layer that includes the compound of Chemical Formula 1may further include one or more compounds selected from the groupconsisting of arylamine-based compounds or styrylarylamine-basedcompounds. The arylamine-based compound or styrylarylamine-basedcompound also includes those illustrated in Korean Patent ApplicationNo. 10-2008-0123276 or Korean Patent Application No. 10-2008-0107606,but is not limited thereto.

In addition, in the organic light emitting device of the presentinvention, the organic material layer that includes the compound ofChemical Formula 1 may further include one or more metals or complexcompounds selected from the group consisting of group 1, group 2, period4 and period 5 transition metals, lanthanide-series metals, and organicmetals of d-transition atoms.

The organic light emitting device according to the present invention maybe manufactured as an organic light emitting device that emits whitelight by further including one or more organic materials that emit blue,red or green light in addition to the compound of Chemical Formula 1.For example, the organic light emitting device may be manufactured toemit white light by including two or more light emitting materials inone organic material layer, or including two or more light emittinglayers that emit different light emitting colors.

The organic light emitting device may include a light emitting layer anda charge generation layer together.

In the organic light emitting device according to the present invention,materials other than the compound of Chemical Formula 1 are illustratedbelow, however, these are for the illustrative purposes only, and do notintend to limit the scope of the present invention, and these materialsmay be substituted with materials known in the related art.

As the anode material, materials having relatively large work functionmay be used, and transparent conductive oxides, metals, conductivepolymers or the like may be used.

As the cathode material, materials having relatively small work functionmay be used, and metals, metal oxides, conductive polymers or the likemay be used.

As the hole transfer material, a pyrazoline derivative, anarylamine-based derivative, a stilbene derivative, a triphenyldiaminederivative or the like may be used, and a low molecular or highmolecular material may also be used.

As the light emitting material, a red, green or blue light emittingmaterial may be used, and when necessary, two or more light emittingmaterials may be mixed and used. In addition, as the light emittingmaterial, a fluorescent material may be used, but a phosphorescentmaterial may also be used. As the light emitting material, materialsthat emit alone by bonding the holes and the electrons injected from ananode and a cathode, respectively, may be used, however, materials inwhich a host material and a dopant material are both involved in lightemitting may also be used.

As the electron transfer material, an oxadiazole derivative,anthraquinodimethane and a derivative thereof, benzoquinone and aderivative thereof, naphthoquinone and a derivative thereof,anthraquinone and a derivative thereof, tetracyanoanthraquinodimethaneand a derivative thereof, a fluorenone derivative,diphenyldicyanoethylene and a derivative thereof, a diphenoquinonederivative, 8-hydroxyquinoline and a metal complex of a derivativethereof, or the like, may be used, and a high molecular material as wellas a low molecular material may also be used.

As the electron injection material, for example, LiF is typically usedin the related industry, however, the present invention is not limitedthereto.

Hereinafter, an organic light emitting compound according to the presentinvention, the preparation method thereof, and light emitting propertiesof the device will be described with reference to representativecompounds of the present invention in order to understand the presentinvention in detail, however, this is only to illustrate theembodiments, and the scope of the present invention is not limited tothese compounds.

Preparation Example 1 Preparation of Compound 1

Preparation of Compound 1-1

After 10 g (42.7 mmol) of dibenzopentalenedione and 22.5 g (108 mmol) ofphosphorus pentachloride were placed in a vessel, the vessel was sealedand heated until a liquid formed, and then an excess acetic acidsolution was added thereto and the result was stirred for 48 hours.After the reaction completed, the compound was filtered using water, andthen the liquid was extracted using water and diethylether. The solutionwas vacuum distilled, and separated and purified using a column,resulting in 5.8 g (16.9 mmol) of Compound 1-1.

Preparation of Compound 1-2

5 g (14.6 mmol) of Compound 1-1 was dissolved in acetic acid, and thenthe mixture was heated under reflux for 4 hours. After the reactioncompleted, the result was extracted using diethylether and water, andrecrystallized using ethyl acetate, resulting in 3 g (14.6 mmol) ofCompound 1-2.

Preparation of Compound 1

A solution in which 6 g (29.4 mmol) of Compound 1-2 and 0.12 ml (4.7mmol) of bromine were dissolved in 300 ml of carbon disulfide wasstirred for 12 hours at 0° C. After the stirring, the carbon disulfidewas removed by vacuum distillation, and 19.6 g (117.5 mmol) of silvernitrate was added thereto. The mixture was dissolved in 250 ml ofbenzene, and the result was heated under reflux for 2 hours. After thereaction completed, the solution was vacuum distilled, and separated andpurified using a column, resulting in 2.8 g (14.1 mmol) of Compound 1.

Preparation Example 2 Preparation of Compound 5

Preparation of Compound 5-1

To a solution in which 337 mg (1.77 mmol) of CuI and 744 mg (1.06 mmol)of Pd(PPh₃)₂Cl₂ were dissolved in 150 ml of triethylamine, 3.2 g (31.8mmol) of phenylacetylene and 10 g (35.3 mml) of 1-bromo-2-iodobenzenewere added in consecutive order, and the mixture was stirred for 24hours at room temperature. After the reaction completed, the result waswashed with an ammonium chloride solution and then extracted using ethylacetate. The solution was vacuum distilled, and separated and purifiedusing a column, resulting in 9 g (35.0 mmol) of Compound 5-1.

Preparation of Compound 5

After 4.3 g (39 mmol) of hydroquinone, 12.67 g (38.9 mmol) of Cs₂CO₃,5.9 g (38.9 mmol) of CsF, 0.12 g (0.59 mmol) of P(t-Bu)₃ and 0.27 g(0.29 mmol) of Pd₂(dba)₃ were placed in a reaction vessel, a solution inwhich 5 g (19.45 mmol) of Compound 5-1 was dissolved in 150 ml of1,4-dioxane was added thereto, and then the mixture was stirred for 24hours at 120° C. After the reaction completed, the reaction solution wasdissolved in toluene and then extracted, and residual water was removedusing magnesium sulfate. The solution was vacuum distilled, andseparated and purified using a column, resulting in 5.5 g (15.5 mmol) ofCompound 5.

Preparation Example 3 Preparation of Compound 6

Preparation of Compound 6-1

A solution in which 15 g (82.4 mmol) of 2-bromobenzonitrile and 16.2 g(98.9 mmol) of PhSOOH were dissolved in 100 ml of DMF was heated underreflux for 2 hours at 80° C. After the reaction completed, the resultwas extracted using ethyl acetate and water, and the solution obtainedwas vacuum distilled. The obtained solid was separated and purifiedusing a column, and 18.0 g (70.0 mmol) of Compound 6-1 was obtained.

Preparation of Compound 6-2

15 g (58.3 mmol) of Compound 6-1, 60 ml of 1M DIBAL solution and 45 mlof dichloromethane was placed in a reaction vessel in consecutive order,and the mixture was stirred for 2 hours at −78° C. After that, an excess1M ammonium chloride solution was added thereto and the result wasstirred for additional 1 hour. After the reaction completed, the resultwas extracted using dichloromethane and a hydrochloric acid solution,and the solution obtained was vacuum distilled. The obtained solid wasseparated and purified using a column, and 12.1 g (46.6 mmol) ofCompound 6-2 was obtained.

Preparation of Compound 6-3

After 10 g (38.4 mmol) of Compound 6-2 and 7 ml (46 mmol) of ClP(O)OEt₂were dissolved in 125 ml of THF, the mixture was stirred for 15 minutesat −78° C. After that, 75 ml of an 1M LiHMDS solution was placed in areaction vessel, and the result was stirred for 2 hours at roomtemperature. After the temperature of the reaction vessel was againlowered to −78° C., 200 ml of an 1M DIBAL solution was added thereto,and the result was stirred for 2 hours at room temperature. After thereaction completed, an ammonium chloride solution was added thereto, theresult was shortly stirred, then the solution was extracted usingdichloromethane, and the liquid obtained was vacuum distilled. Theobtained solid was separated and purified using a column, and 4.6 g (23mmol) of Compound 6-3 was obtained.

Preparation of Compound 6-4

After 5 g (25 mmol) of Compound 6-3 and 4.7 g (27.4 mmol) of IBr weredissolved in 150 ml of dichloromethane, the mixture was stirred for 1hour at −78° C. After the reaction completed, a sodium sulfite solutionwas added thereto, and then the result was shortly stirred. Next, thesolution was extracted using an organic solvent, and the liquid obtainedwas vacuum distilled. The obtained solid was separated and purifiedusing a column, and 6.3 g (15.4 mmol) of Compound 6-4 was obtained.

Preparation of Compound 6-5

After 5 g (12.2 mmol) of Compound 6-4, 3.1 g (18.4 mmol) of 1-naphthylboronic acid, 1.4 g (1.2 mmol) of Pd(PPh₃)₄, and 7.8 g (36.9 mmol) ofK₃PO₄ were dissolved in 37 ml of 1,4-dioxane and 13 ml of water, themixture was heated under reflux for 2 hours at 90° C. After the reactioncompleted, an ammonium chloride solution was added thereto, the solutionwas extracted using an organic solvent, and the liquid obtained wasvacuum distilled. The obtained solid was separated and purified using acolumn, and 4.3 g (10.4 mmol) of Compound 6-5 was obtained.

Preparation of Compound 6

After 6 g (14.7 mmol) of Compound 6-5, 2.7 g (22.1 mmol) ofphenylboronic acid, 1.7 g (1.5 mmol) of Pd(PPh₃)₄ and 9.4 g (44.2 mmol)of K₃PO₄ were dissolved in 45 ml of 1,4-dioxane and 15 ml of water, themixture was heated under reflux for 2 hours at 90° C. After the reactioncompleted, an ammonium chloride solution was added thereto, the solutionwas extracted using an organic solvent, and the liquid obtained wasvacuum distilled. The obtained solid was separated and purified using acolumn, and 5.4 g (13.3 mmol) of Compound 6 was obtained.

Preparation Example 4 Preparation of Compound 66

After 5 g (12.2 mmol) of Compound 6-5, 5.8 g (18.4 mmol) ofphenylboronic acid, 1.4 g (1.2 mmol) of Pd(PPh₃)₄, and 7.8 g (36.9 mmol)of K₃PO₄ were dissolved in 37 ml of 1,4-dioxane and 13 ml of water, themixture was heated under reflux for 2 hours at 90° C. After the reactioncompleted, an ammonium chloride solution was added thereto, the solutionwas extracted using an organic solvent, and the liquid obtained wasvacuum distilled. The obtained solid was separated and purified using acolumn, and 5.5 g (9.2 mmol) of Compound 66 was obtained.

Preparation Example 5 Preparation of Compound 82

Preparation of Compound 82-1

After 4 g (10 mmol) of 2,3,5,6-tetrabromobenzene and 5 ml (70 mmol) offuran were dissolved in 50 ml of THF, 25 ml of a 0.5M n-BuLi solutionwas added thereto at −78° C., and then the mixture was stirred for 18hours. After the reaction completed, small amount of methanol was addedthereto, the result was extracted using an organic solvent, and thesolution obtained was vacuum distilled. The obtained solid wasrecrystallized using hexane and methanol, and 2.0 g (6.5 mmol) ofCompound 82-1 was obtained.

Preparation of Compound 82-2

8.7 g (132 mmol) of zinc powder and 8.7 ml (79 mmol) of titaniumtetrachloride were dissolved in 200 ml of THF, and the mixture washeated under reflux for 18 hours. After the mixture was cooled to roomtemperature, a solution in which 4 g (13.2 mmol) of Compound 82-1 wasdissolved in THF was added thereto, and the result was heated underreflux for 18 hours. After the reaction completed, an HCl solution wasintroduced thereto, the result was extracted using an organic solvent,and the solution obtained was vacuum distilled. The obtained solid wasseparated and purified using a column, and 3.1 g (11.0 mmol) of Compound82-2 was obtained.

Preparation of Compound 82-3

2 g (7.0 mmol) of Compound 82-2, 0.7 g (7.0 mmol) of phenylacetylene,0.3 g (0.3 mmol) of Pd(PPh₃)₂Cl₂ and 4.5 g (21.0 mmol) of CuI wereplaced in a reaction vessel in consecutive order, dissolved in 30 ml oftriethylamine, and the mixture was heated under reflux for 18 hours at100° C. After the reaction completed, an HCl solution was introducedthereto, the result was extracted using an organic solvent, and thenresidual water was removed using sodium sulfate. After the solution wasvacuum distilled, the obtained solid was separated and purified using acolumn, and 1.0 g (3.3 mmol) of Compound 82-3 was obtained.

Preparation of Compound 82

5.5 g (18.0 mmol) of Compound 82-3, 5.9 g (9.0 mmol) of Ni(PPh₃)₂Cl₂ and1.8 g (26.9 mmol) of zinc powder were placed in a reaction vessel inconsecutive order, were dissolved in 80 ml of tetrahydrofuran and 20 mlof diethylether, and the mixture was heated under reflux for 24 hours at80° C. After the reaction completed, the result was extracted using anorganic solvent, and the solution obtained was vacuum distilled. Theobtained solid was separated and purified using a column, and 1.5 g (3.2mmol) of Compound 82 was obtained.

Preparation Example 6 Preparation of Compound 107

Preparation of Compound 107-1

4 g (14.0 mmol) of Compound 82-2, 2.1 g (14.0 mmol) of phenylacetylene,0.5 g (0.7 mmol) of Pd(PPh₃)₂Cl₂ and 8.9 g (42.0 mmol) of CuI wereplaced in a reaction vessel in consecutive order, were dissolved in 60ml of triethylamine, and the mixture was heated under reflux for 18hours at 100° C. After the reaction completed, an HCl solution wasintroduced thereto, the result was extracted using an organic solvent,and then residual water was removed using sodium sulfate. After thesolution was vacuum distilled, the obtained solid was separated andpurified using a column, and 2.1 g (5.9 mmol) of Compound 107-1 wasobtained.

Preparation of Compound 107

4 g (11.2 mmol) of Compound 107-1, 3.7 g (5.6 mmol) of Ni(PPh₃)₂Cl₂ and1.1 g (16.8 mmol) of zinc powder were placed in a reaction vessel inconsecutive order, were dissolved in 48 ml of tetrahydrofuran and 12 mlof diethylether, and the mixture was heated under reflux for 24 hours at80° C. After the reaction completed, the result was extracted using anorganic solvent, and the solution obtained was vacuum distilled. Theobtained solid was separated and purified using a column, and 683 mg(1.2 mmol) of Compound 107 was obtained.

Preparation Example 7 Preparation of Compound 116

Preparation of Compound 116-1

After 10 g (55.2 mmol) of 3-bromophenylacetylene, 14.3 g (82.9 mmol) of2-naphthyl boronic acid, 6.4 g (5.5 mmol) of Pd(PPh₃)₄ and 35.2 g (165mmol) of K₃PO₄ were dissolved in 150 ml of 1,4-dioxane and 50 ml ofwater, the mixture was heated under reflux for 2 hours at 90° C. Afterthe reaction completed, an ammonium chloride solution was added thereto,the solution was extracted using an organic solvent, and the liquidobtained was vacuum distilled. The obtained solid was separated andpurified using a column, and 10.2 g (44.7 mmol) of Compound 116-1 wasobtained.

5

Preparation of Compound 116-2

To a solution in which 417 mg (2.2 mmol) of CuI and 922 mg (1.3 mmol) ofPd(PPh₃)₂Cl₂ were dissolved in 400 ml of triethylamine, 10 g (43.8 mmol)of Compound 116-1 and 12.5 g (43.8 mml) of Compound 82-2 were added inconsecutive order, and the mixture was stirred for 24 hours at roomtemperature. After the reaction completed, the result was washed with anammonium chloride solution, and then extracted using ethyl acetate. Thesolution was vacuum distilled, and then separated and purified using acolumn, resulting in 9 g (43.4 mmol) of Compound 116-2.

Preparation of Compound 116-3

After the temperature of a solution in which 8 g (24.0 mmol) of2-bromo-3-iodonaphthalene was dissolved in 12 ml of tetrahydrofuran waslowered to −78° C., a 2.5M n-BuLi solution was added thereto, and themixture was stirred for 40 minutes. After the reaction vessel was warmedto room temperature, 8.6 g (26.4 mmol) of SnBu₃Cl was added thereto, andthe result was stirred for 18 hours. When the reaction completed, theresult was washed with an ammonium chloride solution, extracted using anorganic solvent, and residual water was removed using magnesium sulfate.The solution was vacuum distilled, and then separated and purified usinga column, resulting in 11.9 g (24.0 mmol) of 116-3.

Preparation of Compound 116-4

To a solution in which 38 mg (0.1 mmol) of CuI and 85 mg (0.1 mmol) ofPd(PPh₃)₂Cl₂ were dissolved in 20 ml of triethylamine, 2 g (4.0 mmol) ofCompound 116-3 and 0.6 g (4.0 mml) of 1-ethynylnaphthalene were added inconsecutive order, and the mixture was stirred for 24 hours at roomtemperature. After the reaction completed, the result was washed with anammonium chloride solution, and then extracted using ethyl acetate. Thesolution was vacuum distilled, and then separated and purified using acolumn, resulting in 2.2 g (3.9 mmol) of Compound 116-4.

Preparation of Compound 116

1.1 g (9.7 mmol) of hydroquinone, 3.2 g (9.7 mmol) of Cs₂CO₃, 1.5 g (9.7mmol) of CsF, 0.03 g (0.15 mmol) of P(t-Bu)₃ and 0.07 g (0.07 mmol) ofPd₂(dba)₃ were placed in a reaction vessel, and after a solution inwhich 2.1 g (4.8 mmol) of Compound 116-2 and 3 g (5.3 mmol) of Compound116-4 were dissolved in 75 ml of 1,4-dioxane was added thereto, themixture was stirred for 24 hours at 150° C. After the reactioncompleted, the reaction solution was dissolved in toluene and thenextracted, and residual water was removed using magnesium sulfate. Thesolution was vacuum distilled, and separated and purified using acolumn, resulting in 1.2 g (1.8 mmol) of Compound 116.

Preparation Example 8 Preparation of Compound 139 Preparation ofCompound 139-1

To a solution in which 0.17 g (0.9 mmol) of CuI and 0.37 g (0.5 mmol) ofPd(PPh₃)₂Cl₂ were dissolved in 400 ml of triethylamine, 5 g (17.5 mmol)of 1,2-dibromonaphthalene and 2.7 g (17.5 mml) of 2-ethynylnaphthalenewere added in consecutive order, and the mixture was stirred for 24hours at room temperature. After the reaction completed, the result waswashed with an ammonium chloride solution, and then extracted usingethyl acetate. The solution was vacuum distilled, and then separated andpurified using a column, resulting in 3 g (8.4 mmol) of Compound 139-1.

Preparation of Compound 139-2

To a solution in which 0.17 g (0.9 mmol) of CuI and 0.37 g (0.5 mmol) ofPd(PPh₃)₂Cl₂ were dissolved in 400 ml of triethylamine, 5 g (17.5 mmol)of 1,2-dibromonaphthalene and 1.8 g (17.5 mml) of phenylacetylene wereadded in consecutive order, and the mixture was stirred for 24 hours atroom temperature. After the reaction completed, the result was washedwith an ammonium chloride solution, and then extracted using ethylacetate. The solution was vacuum distilled, and then separated andpurified using a column, resulting in 2.3 g (7.3 mmol) of Compound139-2.

Preparation of Compound 139

1.3 g (11.8 mmol) of hydroquinone, 3.8 g (11.8 mmol) of Cs₂CO₃, 1.8 g(11.8 mmol) of CsF, 0.03 g (0.17 mmol) of P(t-Bu)₃ and 0.08 g (0.09mmol) of Pd₂(dba)₃ were placed in a reaction vessel, and after asolution in which 2 g (4.8 mmol) of Compound 139-1 and 2 g (5.3 mmol) ofCompound 139-2 were dissolved in 60 ml of 1,4-dioxane was added thereto,the mixture was stirred for 24 hours at 150° C. After the reactioncompleted, the reaction solution was dissolved in toluene and thenextracted, and residual water was removed using magnesium sulfate. Thesolution was vacuum distilled, and separated and purified using acolumn, resulting in 1.5 g (3.0 mmol) of Compound 139.

Preparation Example 9 Preparation of Compound 163 Preparation ofCompound 163-1

To a solution in which 0.17 g (0.9 mmol) of CuI and 0.37 g (0.5 mmol) ofPd(PPh₃)₂Cl₂ were dissolved in 400 ml of triethylamine, 5 g (17.5 mmol)of 1,2-dibromonaphthalene and 3.5 g (17.5 mml) of 9-ethynylanthracenewere added in consecutive order, and the mixture was stirred for 24hours at room temperature. After the reaction completed, the result waswashed with an ammonium chloride solution, and then extracted usingethyl acetate. The solution was vacuum distilled, and then separated andpurified using a column, resulting in 2.8 g (6.8 mmol) of Compound163-1.

Preparation of Compound 163-2

To a solution in which 0.17 g (0.9 mmol) of CuI and 0.37 g (0.5 mmol) ofPd(PPh₃)₂Cl₂ were dissolved in 400 ml of triethylamine, 5 g (17.5 mmol)of 1,2-dibromonaphthalene and 2.7 g (17.5 mml) of 1-ethynylnaphthalenewere added in consecutive order, and the mixture was stirred for 24hours at room temperature. After the reaction completed, the result waswashed with an ammonium chloride solution, and then extracted usingethyl acetate. The solution was vacuum distilled, and then separated andpurified using a column, resulting in 2.9 g (8.2 mmol) of Compound163-2.

Preparation of Compound 163

1.7 g (15.2 mmol) of hydroquinone, 5.0 g (15.2 mmol) of Cs₂CO₃, 2.3 g(15.2 mmol) of CsF, 0.05 g (0.23 mmol) of P(t-Bu)₃ and 0.10 g (0.11mmol) of Pd₂(dba)₃ were placed in a reaction vessel, and after asolution in which 3.1 g (7.6 mmol) of Compound 163-1 and 3 g (8.4 mmol)of Compound 163-2 were dissolved in 100 ml of 1,4-dioxane was addedthereto, the mixture was stirred for 24 hours at 150° C. After thereaction completed, the reaction solution was dissolved in toluene andthen extracted, and residual water was removed using magnesium sulfate.The solution was vacuum distilled, and separated and purified using acolumn, resulting in 1.8 g (3.0 mmol) of Compound 163.

Preparation Example 10 Preparation of Compound 206 Preparation ofCompound 206-1

To a solution in which 0.1 g (0.5 mmol) of CuI and 0.22 g (0.3 mmol) ofPd(PPh₃)₂Cl₂ were dissolved in 200 ml of triethylamine, 3 g (10.5 mmol)of 1,2-dibromonaphthalene and 1.6 g (10.5 mml) of 2-ethynylnaphthalenewere added in consecutive order, and the mixture was stirred for 24hours at room temperature. After the reaction completed, the result waswashed with an ammonium chloride solution, and then extracted usingethyl acetate. The solution was vacuum distilled, and then separated andpurified using a column, resulting in 1.6 g (4.5 mmol) of Compound206-1.

Preparation of Compound 206-2

To a solution in which 0.1 g (0.5 mmol) of CuI and 0.22 g (0.3 mmol) ofPd(PPh₃)₂Cl₂ were dissolved in 200 ml of triethylamine, 3 g (10.5 mmol)of 1,2-dibromonaphthalene and 1.6 g (10.5 mml) of 1-ethynylnaphthalenewere added in consecutive order, and the mixture was stirred for 24hours at room temperature. After the reaction completed, the result waswashed with an ammonium chloride solution, and then extracted usingethyl acetate. The solution was vacuum distilled, and then separated andpurified using a column, resulting in 1.2 g (3.3 mmol) of Compound206-2.

Preparation of Compound 206

1.1 g (10.1 mmol) of hydroquinone, 3.3 g (10.1 mmol) of Cs₂CO₃, 1.5 g(10.1 mmol) of CsF, 0.04 g (0.2 mmol) of P(t-Bu)₃ and 0.07 g (0.08 mmol)of Pd₂(dba)₃ were placed in a reaction vessel, and after a solution inwhich 1.8 g (5.0 mmol) of Compound 206-1 and 2 g (5.5 mmol) of Compound206-2 were dissolved in 100 ml of 1,4-dioxane was added thereto, themixture was stirred for 24 hours at 150° C. After the reactioncompleted, the reaction solution was dissolved in toluene and thenextracted, and residual water was removed using magnesium sulfate. Thesolution was vacuum distilled, and separated and purified using acolumn, resulting in 1.1 g (2.0 mmol) of Compound 206.

Preparation Example 11 Preparation of Compound 244 Preparation ofCompound 244-1

To a solution in which 0.07 g (0.4 mmol) of CuI and 0.15 g (0.2 mmol) ofPd(PPh₃)₂Cl₂ were dissolved in 60 ml of triethylamine, 2 g (7.0 mmol) of1-bromo-2-iodobenzene and 1.1 g (7.0 mml) of 1-ethynylnaphthalene wereadded in consecutive order, and the mixture was stirred for 24 hours atroom temperature. After the reaction completed, the result was washedwith an ammonium chloride solution, and then extracted using ethylacetate. The solution was vacuum distilled, and then separated andpurified using a column, resulting in 1.7 g (5.6 mmol) of Compound244-1.

Preparation of Compound 244-2

To a solution in which 0.07 g (0.4 mmol) of CuI and 0.15 g (0.2 mmol) ofPd(PPh₃)₂Cl₂ were dissolved in 80 ml of triethylamine, 2 g (7.0 mmol) of1,2-dibromonaphthalene and 1.7 g (7.0 mml) of9,9-diethyl-2-ethynyl-9H-fluorene were added in consecutive order, andthe mixture was stirred for 24 hours at room temperature. After thereaction completed, the result was washed with an ammonium chloridesolution, and then extracted using ethyl acetate. The solution wasvacuum distilled, and then separated and purified using a column,resulting in 1.1 g (2.5 mmol) of Compound 244-2.

Preparation of Compound 244

1.3 g (11.2 mmol) of hydroquinone, 3.8 g (11.2 mmol) of Cs₂CO₃, 1.8 g(11.2 mmol) of CsF, 0.04 g (0.18 mmol) of P(t-Bu)₃ and 0.08 g (0.09mmol) of Pd₂(dba)₃ were placed in a reaction vessel, and after asolution in which 1.8 g (5.9 mmol) of Compound 244-1 and 2.9 g (6.4mmol) of Compound 244-2 were dissolved in 60 ml of 1,4-dioxane was addedthereto, the mixture was stirred for 24 hours at 150° C. After thereaction completed, the reaction solution was dissolved in toluene andthen extracted, and residual water was removed using magnesium sulfate.The solution was vacuum distilled, and separated and purified using acolumn, resulting in 1.5 g (2.6 mmol) of Compound 244.

In addition, various compounds represented by Chemical Formulae 1 to 6may be synthesized by introducing various substituents using well-knownmethods with any one, two or more mixtures selected from2,4-dichloropyrido[2,3-d]pyrimidine (manufactured by OChemIncorporation), 2-chloro-pyrido[3,2-d]pyrimidine (manufactured byAnichem LLC), pyrido[4,3-d]pyrimidin-4(3H)-one (manufactured by AcesPharma, Inc.), 2-chloro-6,7-dimethyl-pteridine (manufactured byInternational Laboratory Limited), 2-chloropteridine (manufactured byPrinceton BioMolecular Research, Inc.), 3-chloroquinoline (manufacturedby Texas Biochemicals Inc.), 2,4-dichloroquinoline (manufactured byShanghai PI Chemicals Ltd), 2,3-dichloroquinoline (manufactured by AcesPharma, Inc.), 1-chloroisoquinoline (manufactured by Alfa Aesar, ChinaLtd.), 1,3-dichloroisoquinoline (manufactured by Aalen Chemical Co.Ltd.) and 1,4-dichloroisoquinoline (manufactured by Bepharm Ltd) as astarting material.

Compound 1 to Compound 285 were prepared using the methods ofPreparation Examples 1 to 11, and ¹H NMR and MS/FAB of the preparedcompounds are shown in Table 1.

TABLE 1 MS/FAB Compound ¹H NMR (CDCl₃, 200 MHz) Found Calculated 1 δ =8.42 (4H, d), 8.10 (4H, d) 202.25 202.08 3 δ = 8.42 (4H, d), 8.10 (4H,d), 2.34 (6H, s) 230.30 230.11 5 δ = 7.68 (4H, d), 7.54 (4H, t), 7.47(2H, 354.14 354.14 t), 7.21 (2H, d), 7.03 (2H, d), 6.92 (2H, t), 6.85(2H, t) 6 δ = 8.55 (1H, d), 8.42 (5H, d), 8.10 (4H, d), 404.50 404.168.08 (1H, d), 8.04 (1H, d), 7.61 (1H, t), 7.55 (2H, d), 7.52 (2H, d),7.51 (2H, t), 7.41 (1H, t) 10 δ = 8.93 (2H, d), 8.55 (1H, d), 8.42 (4H,d), 454.56 454.17 8.12 (2H, t), 8.10 (4H, d), 7.93 (1H, d), 7.88~7.82(4H, m), 7.52 (2H, d), 7.51 (2H, t), 7.41 (1H, t) 13 δ = 8.55 (1H, d),8.42 (4H, d), 8.12 (1H, d), 443.54 443.17 8.10 (4H, d), 7.94 (1H, d),7.63~7.25 (10H, m) 16 δ = 8.42 (4H, d), 8.10 (4H, d), 7.70 (1H, s),430.54 430.17 7.57 (1H, t), 7.52 (4H, d), 7.51 (4H, t), 7.48 (2H, d),7.41 (2H, t) 19 δ = 8.42 (4H, d), 8.10 (4H, d), 8.00 (2H, d), 480.60480.19 7.92 (1H, d), 7.73~7.48 (12H, m) 7.41 (1H, t) 21 δ = 8.42 (4H,d), 8.10 (4H, d), 7.83 (1H, s), 392.49 392.16 7.52 (4H, d), 7.51 (4H,t), 7.41 (2H, t), 7.21 (2H, d), 6.58 (1H, d), 6.39 (1H, ds), 3.22 (1H,d), 24 δ = 8.42 (5H, d), 8.10 (4H, d), 7.96 (1H, t), 428.52 428.16 7.90(1H, d), 7.80 (1H, d), 7.58 (1H, t), 7.52 (2H, d), 7.51 (2H, t), 7.41(1H, t), 7.15 (2H, s) 27 δ = 8.55 (2H, d), 8.42 (4H, d), 8.10 (4H, d),480.60 480.19 8.01 (2H, s), 7.55 (2H, d), 7.52 (2H, d), 7.51 (4H, t),7.49 (2H, d), 7.41 (2H, t) 30 δ = 8.42 (4H, d), 8.10 (4H, d), 7.92 (2H,d), 480.60 480.19 7.73 (2H, d), 7.58 (2H, s), 7.52 (4H, d), 7.51 (4H,t), 7.41 (2H, t) 32 δ = 8.42 (4H, d), 8.10 (4H, d), 8.06 (1H, s), 546.70546.23 7.87~7.53 (4H, m), 7.52 (4H, d), 7.51 (4H, t), 7.41 (2H, t),7.38~7.28 (4H, s), 1.72 (6H, s) 35 δ = 8.55 (1H, d), 8.42 (4H, d), 8.10(4H, d), 519.63 519.20 7.98~7.69 (4H, m), 7.58 (2H, t), 7.52 (6H, m),7.45 (1H, t), 7.41 (1H, t), 7.33~7.25 (2H, d) 41 δ = 8.55 (2H, d), 8.42(6H, d), 8.10 (4H, d), 454.56 454.17 8.06 (4H, d), 7.61 (2H, t), 7.55(4H, d) 45 δ = 8.93 (2H, d), 8.55 (1H, d), 8.42 (5H, d), 504.62 504.198.12 (2H, d), 8.10 (4H, d), 8.06 (2H, d), 7.93 (1H, d), 7.85 (4H, t),7.61 (1H, t), 7.55 (2H, d) 47 δ = 8.55 (2H, d), 8.42 (5H, d), 8.10 (4H,d), 520.66 520.22 8.06 (2H, d), 7.90 (2H, dd), 7.77~7.55 (6H, m),7.38~7.28 (2H, m), 1.72 (6H, s) 50 δ = 8.55 (2H, d), 8.42 (5H, d), 8.10(4H, d), 480.60 480.19 8.06 (2H, d), 7.61 (1H, t), 7.55 (2H, d), 7.52(4H, dt), 7.41 (1H, t), 7.25 (4H, s) 52 δ = 8.55 (2H, d), 8.42 (6H, d),8.10 (4H, d), 530.66 530.20 8.06 (4H, d), 7.61 (2H, t), 7.55 (4H, d),7.25 (4H, s) 57 δ = 8.55 (1H, d), 8.42 (5H, d), 8.10 (4H, d), 442.55442.17 8.06 (2H, d), 7.61 (1H, t), 7.55 (2H, d), 7.33 (1H, d), 7.26 (1H,d), 7.21 (2H, t), 6.94 (1H, s), 3.22 (1H, s) 59 δ = 8.55 (1H, d), 8.42(5H, d), 8.10 (4H, d), 478.58 478.17 8.06 (2H, d), 7.96~7.79 (4H, d),7.61 (1H, t), 7.58 (1H, t), 7.55 (2H, d), 7.15 (2H, s) 66 δ = 8.55 (1H,d), 8.42 (5H, d), 8.10 (4H, d), 596.76 596.25 8.06 (2H, d), 7.61 (1H,t), 7.58 (1H, t), 7.55 (2H, d), 7.25 (4H, s) 69 δ = 8.55 (1H, d), 8.42(5H, d), 8.10 (4H, d), 569.69 569.21 8.08 (1H, d), 8.04 (1H, d), 7.87(2H, d), 7.77 (2H, s), 7.69 (2H, d), 7.61 (1H, t), 7.55 (2H, d), 7.52(2H, d), 7.51 (2H, t) 7.41 (1H, t) 71 δ = 8.55 (1H, d), 8.42 (5H, d),8.18 (1H, d), 645.79 645.25 8.10 (4H, d), 8.08 (1H, d), 8.04 (1H, d),8.00 (1H, d), 7.87 (1H, d), 7.77 (2H, s), 7.69 (1H, d), 7.58 (2H, t),7.55 (2H, d), 7.52 (2H, d), 7.51 (2H, t), 7.50 (2H, d), 7.45 (2H, d),7.41 (1H, d) 76 δ = 8.55 (1H, d), 8.42 (5H, d), 8.10 (4H, d), 571.71571.23 8.08 (1H, d), 8.04 (1H, d), 7.61 (1H, d), 7.55 (2H, d), 7.54 (2H,d), 7.20 (4H, t), 6.81 (2H, d), 6.69 (2H, d), 6.63 (4H, d) 79 δ = 8.16(4H, d), 7.67 (8H, d) 302.37 302.11 82 δ = 8.16 (4H, d), 7.67 (8H, d),2.34 (2H, s) 330.42 330.14 86 δ = 8.31 (2H, s), 8.16 (4H, d), 7.91 (2H,d), 554.68 554.20 7.87 (1H, d), 7.67 (8H, d), 7.61 (1H, d), 7.52 (2H,d), 7.51 (2H, t), 7.45 (1H, t), 7.41 (1H, t), 7.39 (2H, d) 87 δ = 8.27(1H, s), 8.16 (4H, d), 7.91 (4H, d), 554.68 554.20 7.67 (8H, d), 7.52(2H, d), 7.51 (2H, t), 7.41 (1H, t), 7.39 (4H, d) 90 δ = 8.16 (4H, d),7.93 (1H, d), 7.87 (1H, d), 570.72 570.23 7.77 (1H, s), 7.67 (8H, d),7.63 (1H, d), 7.55 (1H, d), 7.52 (2H, d), 7.51 (2H, t), 7.41 (1H, t),7.38 (1H, t), 7.28 (1H, t), 1.72 (2H, s) 93 δ = 8.16 (4H, d), 8.00 (2H,d), 7.92 (1H, d), 580.71 580.22 7.73 (1H, d), 7.70 (1H, s), 7.67 (8H,d), 7.59 (2H, d), 7.58 (1H, s), 7.57 (1H. t), 7.52 (2H, d), 7.51 (2H,t), 7.48 (2H, d), 7.41 (1H, t) 96 δ = 8.16 (4H, d), 7.67 (8H, d), 7.52(2H, d), 492.61 492.19 7.51 (2H, t), 7.41 (1H, t), 7.33 (1H, d), 7.26(1H, d), 7.21 (2H, d), 6.94 (1H. s), 3.22 (1H, s) 100 δ = 8.16 (4H, d),7.90 (2H, d), 7.79 (2H, d), 578.70 578.20 7.67 (8H, d), 7.63 (1H, d),7.58 (2H, t), 7.52 (2H, d), 7.51 (2H, t), 7.48 (1H, s), 7.41 (1H, t),7.19 (1H, d) 105 δ = 8.18 (1H, d), 8.16 (4H, d), 8.01 (1H, d), 511.63511.24 7.67 (8H, d), 7.53 (2H, d), 7.52 (2H, d), 7.51 (2H, t), 7.41 (1H,t) 107 δ = 8.55 (2H, d), 8.42 (2H, d), 8.16 (4H, d), 554.68 554.20 8.08(2H, d), 8.04 (2H, d), 7.67 (8H, d), 7.61 (2H, d), 7.55 (4H, d) 110 δ =8.55 (1H, s), 8.42 (1H, d), 8.27 (1H, s), 604.74 604.22 8.16 (4H, d),8.08 (1H, d), 8.04 (1H, d), 7.91 (4H, d), 7.67 (8H, d), 7.61 (1H, d),7.55 (2H, d), 7.39 (4H, d) 115 δ = 8.55 (1H, s), 8.42 (1H, d), 8.16 (4H,d), 593.71 593.21 8.12 (1H, d), 8.08 (1H, d), 8.04 (1H, d), 7.87 (1H,d), 7.77 (1H, s), 7.69 (1H, d), 7.67 (8H, d), 7.63 (1H, d), 7.61 (1H,d), 7.55 (2H, d), 7.50 (1H, t), 7.29 (1H, t) 116 δ = 8.55 (1H, d), 8.42(1H, d), 8.16 (4H, d), 630.77 630.23 8.08 (1H, d), 8.04 (1H, d), 8.00(2H, d), 7.92 (1H, d), 7.73 (1H, d), 7.70 (1H, s), 7.67 (8H, d), 7.61(1H, d), 7.59 (2H, d), 7.58 (1H, s), 7.57 (1H, t), 7.55 (2H, d), 7.48(2H, d) 119 δ = 8.55 (1H, d), 8.42 (1H, d), 8.16 (4H, d), 542.67 542.208.08 (1H, d), 8.04 (1H, d), 7.67 (8H, d), 7.61 (1H, d), 7.55 (2H, d),7.33 (1H, d), 7.26 (1H, d), 7.21 (2H, d), 6.94 (1H, s), 3.22 (1H, s) 124δ = 8.55 (2H, d), 8.42 (1H, d), 8.16 (4H, d), 669.81 669.25 8.08 (1H,d), 8.04 (1H, d), 7.94 (1H, d), 7.87 (1H, d), 7.77 (1H, s), 7.69 (1H,d), 7.67 (8H, d), 7.61 (1H, d), 7.58 (2H, d), 7.55 (2H, t), 7.50 (2H,d), 7.45 (1H, t), 7.33 (1H, t), 7.25 (1H, t) 126 δ = 8.55 (1H, d), 8.42(1H, d), 8.16 (4H, d), 543.65 543.20 8.08 (1H, d), 8.04 (1H, d), 7.67(8H, d), 7.61 (1H, d), 7.55 (2H, d), 7.33 (1H, t), 7.26 (1H, t), 7.23(1H, d), 7.01 (1H, d), 3.05 (1H, d) 132 δ = 8.54 (2H, d), 8.16 (4H, d),7.81 (2H, d), 378.46 378.14 7.67 (4H, d), 7.52 (2H, d), 7.51 (2H, t),7.41 (1H, t) 136 δ = 8.55 (1H, d), 8.54 (2H, d), 8.42 (1H, d), 442.55442.17 8.16 (4H, d), 8.08 (1H, d), 8.04 (1H, d), 7.81 (2H, d), 7.67 (4H,d), 7.61 (1H, d), 7.55 (2H, d), 2.34 (1H, s) 139 δ = 8.54 (2H, d), 8.16(4H, d), 8.00 (2H, d), 504.62 504.19 7.92 (1H, d), 7.81 (2H, d), 7.73(1H, d), 7.67 (4H, d), 7.59 (2H, d), 7.58 (1H, s), 7.52 (2H, d), 7.51(2H, t), 7.41 (1H, t) 142 δ = 8.93 (2H, d), 8.54 (2H, d), 8.16 (4H, d),554.68 554.20 8.12 (1H, d), 7.93 (1H, s), 7.88 (2H, t), 7.82 (2H, dt),7.81 (2H, d), 7.67 (4H, d), 7.52 (2H, d), 7.51 (2H, t), 7.41 (1H, t) 147δ = 8.54 (2H, d), 8.16 (4H, d), 8.00 (2H, d), 580.71 580.22 7.92 (1H,d), 7.81 (2H, d), 7.73 (1H, d), 7.70 (1H, s), 7.67 (4H, d), 7.59 (3H,s), 7.57 (1H, t), 7.52 (2H, d), 7.51 (2H, t), 7.48 (2H, d), 7.41 (1H, t)150 δ = 8.54 (2H, d), 8.16 (4H, d), 7.81 (2H, d), 492.61 492.19 7.67(4H, d), 7.52 (2H, d), 7.51 (2H, t), 7.41 (1H, t), 7.33 (1H, d), 7.26(1H, d), 7.21 (2H, d), 6.94 (1H, s), 3.22 (1H, s) 152 δ = 8.54 (2H, d),8.16 (4H, d), 7.96 (1H, d), 528.64 582.19 7.90 (1H, d), 7.81 (2H, d),7.80 (2H, d), 7.67 (4H, d), 7.58 (1H, d) 7.52 (2H, d), 7.51 (2H, t),7.41 (1H, t), 7.15 (2H, s) 158 δ = 8.54 (2H, d), 8.16 (4H, d), 7.81 (2H,d), 495.57 495.16 7.74 (2H, d), 7.67 (4H, d), 7.52 (2H, d), 7.51 (2H,t), 7.41 (1H, t), 7.39 (2H, d) 162 δ = 8.55 (1H, d), 8.54 (2H, d), 8.42(1H, d), 554.68 554.20 8.16 (4H, d), 8.06 (2H, d), 8.00 (2H, d), 7.92(1H, d), 7.81 (2H, d), 7.73 (1H, d), 7.67 (4H, d), 7.61 (1H, t), 7.59(2H, d), 7.58 (1H, d), 7.55 (2H, d) 164 δ = 8.55 (1H, d), 8.54 (2H, d),8.42 (1H, d), 604.74 604.22 8.27 (1H, s), 8.16 (4H, d), 8.06 (2H, d),7.91 (4H, d), 7.81 (2H, d), 7.67 (4H, d), 7.61 (1H, t), 7.55 (2H, d),7.39 (4H, d) 167 δ = 8.55 (1H, d), 8.54 (2H, d), 8.42 (1H, d), 593.71593.21 8.16 (4H, d), 8.06 (2H, d), 7.93 (1H, d), 7.87 (1H, d), 7.81 (2H,d), 7.77 (1H, s), 7.67 (4H, d), 7.63 (1H, d), 7.61 (1H, t), 7.55 (3H,d), 7.38 (1H, t), 7.28 (1H, t), 1.72 (6, s) 171 δ = 8.55 (1H, d), 8.54(2H, d), 8.42 (1H, d), 542.67 542.20 8.16 (4H, d), 8.10 (1H, d), 8.06(2H, d), 7.81 (2H, d), 7.67 (4H, d), 7.61 (1H, t), 7.55 (2H, d), 7.28(2H, d), 6.58 (1H, d), 6.39 (1H, t), 3.22 (1H, d) 176 δ = 8.55 (1H, d),8.54 (2H, d), 8.42 (3H, d), 628.76 628.22 8.16 (4H, d), 8.10 (2H, d),8.06 (2H, d), 7.96 (1H, d), 7.90 (1H, d), 7.81 (3H, d), 7.67 (4H, d),7.61 (1H, t), 7.58 (1H, d), 7.55 (2H, d) 181 δ = 8.55 (1H, d), 8.54 (2H,d), 8.42 (1H, d), 545.63 545.18 8.16 (4H, d), 8.06 (2H, d), 7.81 (2H,d), 7.74 (2H, d), 7.67 (4H, d), 7.61 (1H, t), 7.55 (2H, d), 7.39 (2H, d)183 δ = 8.55 (1H, d), 8.54 (2H, d), 8.42 (1H, d), 671.83 671.26 8.16(4H, d), 8.06 (2H, d), 7.81 (2H, d), 7.67 (4H, d), 7.61 (1H, t), 7.55(2H, d), 7.54 (2H, d), 7.20 (4H, t), 6.81 (2H, t), 6.69 (2H, d), 6.63(4H, d) 189 δ = 8.55 (1H, d), 8.54 (2H, d), 8.42 (1H, d), 454.56 454.178.16 (4H, d), 8.06 (2H, d), 7.81 (2H, d), 7.67 (4H, d), 7.61 (1H, t),7.55 (2H, dt), 7.52 (2H, d), 7.51 (2H, d), 7.41 (1H, t) 194 δ = 8.54(2H, d), 8.16 (4H, d), 7.98 (9H, s), 580.71 580.22 7.81 (2H, d), 7.67(4H, d), 7.52 (2H, d), 7.51 (2H, d), 7.41 (1H, t), 4.82 (2H, s) 196 δ =8.55 (1H, d), 8.54 (2H, d), 8.16 (4H, d), 543.65 543.20 8.12 (1H, d),7.94 (1H, d), 7.81 (2H, d), 7.67 (4H, d), 7.63 (1H, d), 7.52 (2H, d),7.51 (2H, d), 7.50 (1H, t), 7.41 (1H, t), 7.33 (1H, t), 7.29 (1H, d),7.25 (1H, d) 199 δ = 8.54 (2H, d), 8.16 (4H, d), 7.81 (2H, d), 492.61492.19 7.67 (4H, d), 7.52 (2H, d), 7.51 (2H, d), 7.41 (1H, t), 7.33 (1H,d), 7.26 (1H, d), 7.21 (2H, d), 6.94 (1H, s), 3.22 (1H, s) 204 δ = 8.54(2H, d), 8.16 (4H, d), 7.81 (2H, d), 445.51 445.15 7.74 (2H, d), 7.67(4H, d), 7.52 (2H, d), 7.51 (2H, d), 7.41 (1H, t), 7.39 (2H, d) 206 δ =8.55 (1H, d), 8.54 (2H, d), 8.42 (1H, d), 554.68 554.20 8.16 (4H, d),8.06 (2H, d), 8.00 (2H, d), 7.92 (1H, d), 7.81 (2H, d), 7.73 (1H, d),7.67 (4H, d), 7.61 (1H, t), 7.59 (2H, d), 7.58 (1H, s), 7.55 (2H, d) 213δ = 8.55 (1H, d), 8.54 (2H, d), 8.42 (1H, d), 543.65 543.20 8.16 (4H,d), 8.06 (2H, d), 7.81 (2H, d), 7.67 (4H, d), 7.61 (1H, t), 7.55 (2H,d), 7.33 (1H, t), 7.26 (1H, t), 7.23 (1H, d), 7.01 (1H, d), 3.05 (1H, s)217 δ = 8.55 (1H, d), 8.54 (2H, d), 8.42 (3H, dd), 628.76 628.22 8.16(4H, d), 8.10 (2H, d), 8.06 (2H, d), 7.96 (1H, d), 7.90 (1H, d), 7.81(2H, d), 7.80 (1H, d), 7.79 (1H, d), 7.67 (4H, d), 7.61 (1H, t), 7.58(1H, t), 7.55 (2H, d) 220 δ = 8.54 (1H, d), 8.16 (4H, d), 7.81 (1H, d),378.46 378.14 7.67 (6H, ds), 7.52 (2H, d), 7.51 (2H, d), 7.41 (1H, t)222 δ = δ = 8.54 (1H, d), 8.16 (4H, d), 7.81 (1H, 454.56 454.17 d), 7.67(6H, ds), 7.52 (4H, d), 7.51 (4H, d), 7.41 (2H, t) 225 δ = δ = 8.54 (1H,d), 8.31 (2H, s), 8.16 (4H, 554.68 554.20 d), 7.91 (2H, d), 7.87 (1H,d), 7.81 (1H, d), 7.67 (6H, ds), 7.61 (1H, d), 7.52 (2H, d), 7.51 (1H,d), 7.45 (1H, t), 7.41 (1H, t), 7.39 (2H, d) 230 δ = 8.55 (1H, d), 8.54(2H, s), 8.16 (4H, d), 543.65 543.20 8.12 (1H, d), 7.94 (1H, d), 7.81(2H, d), 7.67 (4H, d), 7.63 (1H, d), 7.52 (2H, d), 7.51 (3H, m), 7.41(1H, t), 7.33 (1H, t), 7.27 (2H, t) 233 δ = 8.54 (2H, s), 8.16 (4H, d),7.81 (2H, d), 492.61 492.19 7.67 (4H, d), 7.52 (2H, d), 7.51 (2H, t),7.41 (1H, t), 7.33 (1H, d), 7.26 (1H, d), 7.21 (2H, dd), 6.94 (1H, s),3.22 (1H, s) 238 δ = 8.54 (1H, d), 8.16 (4H, d), 7.81 (1H, d), 495.57495.16 7.74 (2H, d), 7.67 (6H, ds), 7.52 (2H, d), 7.51 (2H, d), 7.41(1H, t), 7.39 (3H, dd) 240 δ = 8.54 (2H, d), 8.42 (1H, d), 8.16 (4H, d),554.68 554.20 8.08 (1H, d), 8.04 (1H, d), 8.00 (2H, d), 7.92 (1H, d),7.81 (1H, t), 7.73 (1H, d), 7.67 (6H, ds), 7.61 (1H, t), 7.59 (2H, d),7.58 (1H, s), 7.55 (2H, d) 244 δ = 8.55 (1H, d), 8.54 (1H, d), 8.42 (3H,dd), 598.77 598.27 8.16 (2H, d), 8.10 (2H, d), 8.06 (2H, dd), 7.93 (1H,d), 7.87 (1H, d), 7.81 (1H, t), 7.77 (1H, s), 7.67 (2H, d), 7.63 (1H,d), 7.61 (1H, t), 7.55 (3H, dd), 7.38 (1H, d), 7.28 (1H, t), 1.91 (4H,d), 0.90 (6H, s) 246 δ = 8.55 (2H, dd), 8.54 (1H, d), 8.42 (3H, dd),619.75 619.23 8.16 (2H, d), 8.10 (2H, d), 8.06 (2H, dd), 7.94 (1H, d),7.87 (1H, d), 7.81 (1H, t), 7.77 (1H, s), 7.69 (1H, d), 7.67 (2H, d),7.61 (1H, t), 7.58 (2H, t), 7.55 (2H, d), 7.50 (2H, d), 7.45 (1H, t),7.33 (1H, t), 7.25 (1H, t) 249 δ = 8.55 (1H, d), 8.42 (3H, d), 8.16 (2H,d), 492.61 492.19 8.10 (2H, d), 8.06 (2H, d), 7.67 (4H, d), 7.61 (1H,t), 7.55 (2H, d), 7.26 (1H, d), 7.21 (2H, t), 7.18 (1H, d), 6.58 (1H,d), 6.39 (1H, d), 4.74 (1H, d) 253 δ = 7.57 (2H, s), 7.45 (2H, d), 7.23(2H, d), 203.30 203.11 2.34 (6H, s) 258 δ = 8.93 (4H, d), 8.12 (4H, d),7.93 (2H, s), 582.73 582.23 7.88 (4H, t), 7.82 (4H, t), 7.57 (2H, s),7.45 (2H, d), 7.23 (2H, d), 2.34 (6H, s) 260 δ = 8.18 (2H, d), 8.12 (2H,d), 8.04 (2H, d), 630.77 630.23 7.88 (2H, d), 7.82 (2H, t), 7.71 (8H,s), 7.57 (2H, s), 7.45 (2H, d), 7.23 (2H, d), 2.34 (6H, s) 265 δ = 7.83(2H, s), 7.57 (2H, s), 7.45 (2H, d), 458.59 458.20 7.24 (2H, d), 7.23(2H, d), 7.21 (2H, d), 6.58 (2H, d), 6.39 (2H, t), 3.22 (2H, s), 2.34(6H, s) 269 δ = 7.52 (4H, d), 7.51 (4H, t), 7.45 (4H, d), 410.55 410.207.41 (2H, t), 2.34 (12H, s) 273 δ = 8.93 (4H, d), 8.12 (4H, d), 7.93(2H, s), 610.78 610.27 7.88 (4H, t), 7.82 (4H, t), 7.45 (4H, d), 2.34(12H, s) 277 δ = 8.55 (2H, d), 8.12 (2H, d), 7.94 (2H, d), 588.74 588.267.63 (2H, d)0, 7.50 (2H, d), 7.45 (4H, d), 7.33 (2H, t), 7.29 (2H, t),7.25 (2H, t), 2.34 (12H, s) 281 δ = 7.45 (4H, d), 7.26 (2H, d), 7.21(4H, dd), 486.64 486.23 7.18 (2H, d), 6.58 (2H, t), 6.39 (2H, t), 4.74(2H, d), 2.34 (12H, s) 285 δ = 8.93 (6H, ds), 8.12 (6H, ds), 7.88 (4H,t), 654.79 654.23 7.82 (4H, t), 7.52 (4H, d), 7.51 (4H, t), 7.41 (2H, t)

As the verification of Compound 5 of the following Chemical Formula, thefollowing data were verified.

UV: 261, 285 nm

PL: 365 nm

HOMO: −5.7 Ev

LUMO: −3.3 ev

Bg: 2.4 eV

Experimental Example Manufacture of OLED Device

A transparent ITO thin film obtained from an OLED glass (manufactured bySamsung Corning Co. Ltd.) was ultrasonic cleaned usingtrichloroethylene, acetone, ethanol and distilled water in consecutiveorder. An ITO substrate was placed on the substrate folder of a vacuumdeposition apparatus, and was exhausted until the degree of vacuumwithin the chamber reaches 10⁻⁶ torr, and then a hole injection layerhaving a thickness of 200 Å was deposited on the ITO substrate byapplying current to the cells within the vacuum deposition apparatus andthereby evaporating 2-TNATA. A hole transfer layer having a thickness of600 Å was deposited on the hole injection layer by applying current toanother cell and thereby evaporating the followingN,N′-bis(α-naphthyl)-N,N′-diphenyl-4,4′-diamine (NPB). In one cell ofthe vacuum deposition apparatus, the compound prepared in the synthesisexamples described in Table 2, or H1 was placed as a host material, andin another cell, the following dopant material D1 was placed andevaporated by applying current to the cell.

Subsequently, a light emitting layer was deposited to a thickness of 400Å on the hole transfer layer by heating and depositing the two cellstogether with the deposition rate ratio of the dopant to be 5% by weight(host:dopant=95:5). Next, the followingtris(8-hydroxyquinoline)aluminum(III) (Alq) was deposited to thicknessof 200 Å as an electron transfer layer. After that, the followinglithium fluoride (LiF) compound was deposited to a thickness of 10 Å asan electron injection layer. Next, an OLED was manufactured bydepositing Al cathode to a thickness of 1000 Å. Meanwhile, the OLED wasmanufactured by purifying each of all the organic compound materialsnecessary for the manufacture of the OLED device through vacuumsublimation purification under 10⁻⁶ to 10⁻⁸ torr.

Test Example Evaluation of OLED Device Characteristics

The results of the current density and the life span of the OLED devicemanufactured in Experimental Examples 1 to 50 and Comparative Example 1,which were measured at 1000 cd/m² and 50% efficiency, are as shown inthe following Table 2.

TABLE 2 No Compound No. Cd/A @1000 cd/m² Life Span (T50) H1 4.5 250 1 14.7 450 2 3 4.6 440 3 5 4.5 410 4 6 4.8 460 5 10 5.1 500 6 13 5.1 400 716 4.6 410 8 19 4.8 450 9 21 4.8 460 10 24 4.6 430 11 27 4.6 430 12 304.5 410 13 32 4.8 450 14 35 4.9 400 15 41 4.9 470 16 45 4.7 450 17 474.9 430 18 50 4.6 440 19 52 4.8 450 20 57 4.9 460 21 59 4.8 440 22 665.0 400 23 69 4.9 410 24 71 5.1 410 25 76 5.0 400 26 79 4.8 460 27 824.8 450 28 86 4.9 470 29 87 4.9 490 30 90 5.1 430 31 93 5.0 450 32 964.7 440 33 100 4.7 430 34 105 4.7 400 35 107 4.8 460 36 110 4.7 440 37115 4.7 400 38 116 4.9 450 39 119 4.8 440 40 124 5.0 390 41 126 4.9 40042 132 4.7 450 43 136 4.8 430 44 139 4.9 460 45 142 4.8 460 46 147 4.6430 47 150 4.9 460 48 152 4.8 450 49 158 4.9 400 50 162 4.7 460

REFERENCE

-   -   100 Substrate    -   200 Anode    -   300 Organic Material Layer    -   301 Hole Injection Layer    -   302 Hole Transfer Layer    -   303 Light Emitting Layer    -   304 Electron Transfer Layer    -   305 Electron Injection Layer    -   400 Cathode

What is claimed is:
 1. A compound of the following Chemical Formula 1:

wherein, in Chemical Formula 1, R₁ and R₂ are each independentlyhydrogen; halogen; substituted or unsubstituted C₁-C₃₀ alkyl;substituted or unsubstituted C₆-C₃₀ aryl; substituted or unsubstitutedC₆-C₃₀ aryl in which one or more of substituted or unsubstituted C₃-C₃₀cycloalkyl, substituted or unsubstituted C₃-C₃₀ heteroaryl andsubstituted or unsubstituted 5-membered to 7-membered heterocycloalkylare fused; substituted or unsubstituted C₃-C₃₀ heteroaryl; substitutedor unsubstituted C₃-C₃₀ heteroaryl in which one or more of substitutedor unsubstituted C₃-C₃₀ cycloalkyl, a substituted or unsubstitutedC₆-C₃₀ aromatic ring and substituted or unsubstituted 5-membered to7-membered heterocycloalkyl are fused; substituted or unsubstituted5-membered to 7-membered heterocycloalkyl; substituted or unsubstituted5-membered to 7-membered heterocycloalkyl in which one or more ofsubstituted or unsubstituted C₃-C₃₀ heterocycloalkyl, a substituted orunsubstituted C₆-C₃₀ aromatic ring and substituted or unsubstitutedC₃-C₃₀ heteroaryl are fused; substituted or unsubstituted C₃-C₃₀cycloalkyl; substituted or unsubstituted C₃-C₃₀ cycloalkyl in which oneor more of substituted or unsubstituted C₃-C₃₀ heterocycloalkyl, asubstituted or unsubstituted C₆-C₃₀ aromatic ring and substituted orunsubstituted C₃-C₃₀ heteroaryl are fused; cyano; —NR₁₁R₁₂;—SiR₁₃R₁₄R₁₅; —OR₁₆; —SR₁₇; substituted or unsubstituted(C₆-C₃₀)ar(C₁-C₃₀)alkyl; substituted or unsubstituted C₁-C₃₀ alkylamino;C₃-C₃₀ heteroaryl in which —SiR₁₈R₁₉R₂₀ is substituted; substituted orunsubstituted C₆-C₃₀ arylamino; substituted or unsubstituted C₂-C₃₀alkenyl; substituted or unsubstituted C₂-C₃₀ alkynyl; carboxyl; nitro orhydroxy; or form a monocyclic or multicyclic aliphatic ring, or amonocyclic or multicyclic aromatic ring, by being linked to an adjacentsubstituent through C₃-C₃₀ alkylene or C₃-C₃₀ alkenylene that does ordoes not include a fused ring; R₁₁ to R₂₀ are each independentlyhydrogen; substituted or unsubstituted C₁-C₃₀ alkyl; substituted orunsubstituted C₆-C₃₀ aryl; or substituted or unsubstituted C₃-C₃₀heteroaryl, or form a monocyclic or multicyclic aliphatic ring, or amonocyclic or multicyclic aromatic ring, by being linked to an adjacentsubstituent through C₃-C₃₀ alkylene or C₃-C₃₀ alkenylene that does ordoes not include a fused ring; the heterocycloalkyl and heteroarylinclude one or more heteroatoms selected from N, O, S and Si; R₃ to R₁₀are each independently hydrogen or a monovalent organic substituent; andR₃ and R₄, R₄ and R₅, R₅ and R₆, R₇ and R₈, R₈ and R₉ or R₉ and R₁₀ forma monocyclic or multicyclic aliphatic ring, or a monocyclic ormulticyclic aromatic ring, by being linked through C₃-C₃₀ alkylene orC₃-C₃₀ alkenylene that does or does not include a fused ring.
 2. Thecompound of claim 1, wherein R₃ to R₁₀ are each independently hydrogen;halogen; substituted or unsubstituted C₁-C₃₀ alkyl; substituted orunsubstituted C₆-C₃₀ aryl; substituted or unsubstituted C₆-C₃₀ aryl inwhich one or more of substituted or unsubstituted C₃-C₃₀ cycloalkyl,substituted or unsubstituted C₃-C₃₀ heteroaryl and substituted orunsubstituted 5-membered to 7-membered heterocycloalkyl are fused;substituted or unsubstituted C₃-C₃₀ heteroaryl; substituted orunsubstituted C₃-C₃₀ heteroaryl in which one or more of substituted orunsubstituted C₃-C₃₀ cycloalkyl, a substituted or unsubstituted C₆-C₃₀aromatic ring and substituted or unsubstituted 5-membered to 7-memberedheterocycloalkyl are fused; substituted or unsubstituted 5-membered to7-membered heterocycloalkyl; substituted or unsubstituted 5-membered to7-membered heterocycloalkyl in which one or more of substituted orunsubstituted C₃-C₃₀ heterocycloalkyl, a substituted or unsubstitutedC₆-C₃₀ aromatic ring and substituted or unsubstituted C₃-C₃₀ heteroarylare fused; substituted or unsubstituted C₃-C₃₀ cycloalkyl; substitutedor unsubstituted C₃-C₃₀ cycloalkyl in which one or more of substitutedor unsubstituted C₃-C₃₀ heterocycloalkyl, a substituted or unsubstitutedC₆-C₃₀ aromatic ring and substituted or unsubstituted C₃-C₃₀ heteroarylare fused; cyano; —NR₁₁R₁₂; —SiR₁₃R₁₄R₁₅; —OR₁₆; —SR₁₇; substituted orunsubstituted (C₆-C₃₀)ar(C₁-C₃₀)alkyl; substituted or unsubstitutedC₁-C₃₀ alkylamino; C₃-C₃₀ heteroaryl in which —SiR₁₈R₁₉R₂₀ issubstituted; substituted or unsubstituted C₆-C₃₀ arylamino; substitutedor unsubstituted C₂-C₃₀ alkenyl; substituted or unsubstituted C₂-C₃₀alkynyl; carboxyl; nitro or hydroxy; or form a monocyclic or multicyclicaliphatic ring, or a monocyclic or multicyclic aromatic ring, by beinglinked to an adjacent substituent through C₃-C₃₀ alkylene or C₃-C₃₀alkenylene that does or does not include a fused ring.
 3. The compoundof claim 2, wherein, in “substituted or unsubstituted” of R₁ to R₁₀,substituted means being each independently further substituted with oneor more selected from the group consisting of deuterium, halogen, C₁-C₃₀alkyl in which halogen is substituted or unsubstituted, C₆-C₃₀ aryl,C₃-C₃₀ heteroaryl in which C₆-C₃₀ aryl is substituted or unsubstituted,5-membered to 7-membered heterocycloalkyl, 5-membered to 7-memberedheterocycloalkyl in which one or more aromatic rings are fused, C₃-C₃₀cycloalkyl, C₃-C₃₀ cycloalkyl in which one or more aromatic rings arefused, tri(C₁-C₃₀)alkylsilyl, di(C₃-C₃₀)alkyl(C₆-C₃₀)arylsilyl,tri(C₆-C₃₀)arylsilyl, C₂-C₃₀ alkenyl, C₂-C₃₀ alkynyl, cyano, carbazolyl,—NR₃₁R₃₂, —SiR₃₃R₃₄R₃₅, —OR₃₆, —SR₃₇, (C₆-C₃₀)ar(C₁-C₃₀)alkyl,(C₁-C₃₀)alkyl(C₆-C₃₀)aryl, C₁-C₃₀ alkyloxy, C₁-C₃₀ alkylthio, C₆-C₃₀aryloxy, C₆-C₃₀ arylthio, carboxyl, nitro or hydroxy, and R₃₁ to R₃₇ areeach independently hydrogen, C₁-C₃₀ alkyl, C₆-C₃₀ aryl or C₃-C₃₀heteroaryl, or form a monocyclic or multicyclic aliphatic ring, or amonocyclic or multicyclic aromatic ring, by being linked to an adjacentsubstituent through C₃-C₃₀ alkylene or C₃-C₃₀ alkenylene that does ordoes not include a fused ring.
 4. The compound of claim 1, wherein R₁ toR₁₀ are each independently selected from hydrogen; halogen; methyl;ethyl; propyl; butyl; pentyl; hexyl; ethylhexyl; heptyl; octyl; phenyl;naphthyl; fluorenyl; biphenyl; phenanthryl; terphenyl; pyrenyl;perylenyl; spirobifluorenyl; fluoranthenyl; chrysenyl; triphenylenyl;1,2-dihydroacenaphthyl; dibenzothiophenyl; dibenzofuryl; carbazolyl;pyridyl; furyl; thienyl; quinolyl; triazinyl; pyrimidinyl; pyridazinyl;quinoxalinyl; phenanthrolinyl; benzopyrrolidino; benzopiperidino;dibenzomorpholino; dibenzoazepino; amino substituted by phenyl,naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl,perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl,dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl,quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl orphenanthrolinyl; biphenyloxy; biphenylthio; biphenylmethyl;triphenylmethyl; carboxyl; nitro or hydroxy.
 5. The compound of claim 1,wherein at least one of R₁ and R₂ is a substituent having seven or morecarbons in ring members, a substituent including two or more rings, orC₁-C₃₀ alkyl.
 6. The compound of claim 1, wherein R₁ and R₂ aredifferent from each other.
 7. The compound of claim 1, wherein ChemicalFormula 1 is represented by any one of Chemical Formulae 2 to 9:

wherein, in Chemical Formulae 2 to 9, R₁, R₂, R₃ and R₄ are the same asthose defined in claim 1, p and q each independently represent aninteger of 1 to 4, Y1 to Y4 represent one of substituted orunsubstituted C₃-C₃₀ cycloalkyl, substituted or unsubstituted C₃-C₃₀heteroaryl, substituted or unsubstituted 5-membered to 7-memberedheterocycloalkyl and substituted or unsubstituted C₆-C₃₀ aryl, or a ringin which two or more of these rings are fused.
 8. The compound of claim1 selected from the following structural formulae:


9. An organic light emitting device comprising: a first electrode; asecond electrode; and one or more organic material layers providedbetween the first electrode and the second electrode, wherein one ormore layers of the organic material layers include the compound ofChemical Formula 1 of claim
 1. 10. The organic light emitting device ofclaim 9, wherein the organic material layer that includes the compoundof Chemical Formula 1 is a light emitting layer.
 11. The organic lightemitting device of claim 9, wherein the organic material layer thatincludes the compound of Chemical Formula 1 further includes afluorescent dopant.
 12. The organic light emitting device of claim 9,wherein the organic material layer that includes the compound ofChemical Formula 1 further includes a blue fluorescent dopant.
 13. Theorganic light emitting device of claim 9, wherein the organic materiallayer that includes the compound of Chemical Formula 1 further includesa phosphorescent dopant.
 14. The organic light emitting device of claim9, wherein the organic material layer that includes the compound ofChemical Formula 1 further includes one or more compounds selected fromthe group consisting of arylamine-based compounds orstyrylarylamine-based compounds.
 15. The organic light emitting deviceof claim 9, wherein the organic material layer that includes thecompound of Chemical Formula 1 further includes one or more metals orcomplex compounds selected from the group consisting of group 1, group2, period 4 and period 5 transition metals, lanthanide-series metals,and organic metals of d-transition atoms.
 16. The organic light emittingdevice of claim 9, further comprising: one or more organic materialsemitting blue, red or green light, in addition to the compound ofChemical Formula
 1. 17. The organic light emitting device of claim 9,further comprising: one or more organic material layers emitting blue,red or green light, in addition to the organic material layer includingthe compound of Chemical Formula
 1. 18. The organic light emittingdevice of claim 9, which emits white light.